Stabilized organic material

ABSTRACT

o-Hydroxyphenyl-s-triazines of the formula I                    
     in which n is 1 to 4 and R 1  to R 7  are as defined in claim  1 , can be used, in combination with sterically hindered amines of the polyalkylpiperidine type, for stabilizing organic polymers. Some of these compounds are novel and can also be used without polyalkylpiperidine.

This is a divisional of U.S. app. Ser. No. 08/591,419, filed Jan. 19,1996, now U.S. Pat. No. 6,187,919, which is a divisional of U.S. app.Ser. No. 08/143,525, filed Oct. 26, 1993, now U.S. Pat. No. 5,736,597,which is a continuation of U.S. app. Ser. No. 07/978,064, filed Nov. 18,1992, abandoned, which is a continuation of U.S. app. Ser. No.07/611,207, filed Nov. 8, 1990, abandoned, which is acontinuation-in-part of U.S. app. Ser. No. 07/446,369, filed Dec. 5,1989, abandoned.

The present invention relates to an organic material containing, asstabilizers, a mixture of a sterically hindered amine and ano-hydroxyphenyl-s-triazine, and to novel o-hydroxyphenyl-s-triazine.

It is already known from U.S. Pat. No. 4,619,956 that polymers can bestabilized against the action of light, moisture and oxygen by adding amixture of a sterically hindered amine and ano-hydroxyphenyl-s-triazine. The triazines used in this context containat least one phenyl group carrying a hydroxyl group in the o-position.

Triazine compounds of this type are relatively sparingly soluble in manysubstrates and tend to migrate. In accordance with the presentinvention, similar triazine derivatives which have an improvedcompatibility with or solubility in organic polymers are used.

The invention relates to an organic material which has been stabilizedagainst damage caused by light, heat and oxygen and which contains

(a) at least one sterically hindered amine of the polyalkylpiperidinetype and

(b) at least one o-hydroxyphenyl-s-triazine, wherein the triazinecompound (b) is a compound of the formula I

 in which n is 1 to 4,

R₁ and R₂ independently of one another are H, OH, C₁-C₁₂alkyl,cyclohexyl or trifluoromethyl,

R₃ and R₄ independently of one another are H, OH, C₁-C₁₂alkyl,cyclohexyl, C₁-C₁₈alkoxy or halogen and, in the event that n=1, can alsobe a radical —OR₇,

R₅ and R₆ independently of one another are H, C₁-C₁₂alkyl or halogen,

R₇, if n is 1, is a) C₁-C₁₈alkyl which is substituted by one or more ofthe groups OH, C₁-C₁₈alkoxy, C₃-C₁₈alkenoxy, haloen, phenoxy (which isunsubstituted or substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen),furyloxy,

 —COOH, —COOR₈, —CONH₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, —NHR₉,—N(R₉)(R₁₀), —NHCOR₁₁, —CN and/or by —O—CO—R₁₁,

b) C₄-C₅₀alkyl which is interrupted by one or more O and can besubstituted by OH or/and glycidyloxy,

c) C₃-C₆alkenyl,

d) glycidyl or a group

e) cyclohexyl which is unsubstituted or substituted by OH or —OCOR₁₁,

f) C₇-C₁₁phenylalkyl which is unsubstituted or substituted by OH, Cl orCH₃,

g) —CO—R₁₂ or

h) —SO₂—R₁₃,

 and if n is 2, R₇ is a) C₂-C₁₆alkylene,

b) C₄-C₁₂alkenylene,

c) xylylene,

d) C₃-C₂₀akylene which is interrupted by one or more O and/orsubstituted by OH,

e) a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—,—CO—NH—R₁₇—NH—CO— or —(CH₂)_(m)—COO—R₁₈—OOC—(CH₂)_(m)— (in which m is 1to 3) or

 and if n is 3, R₇ is a group

 and if n is 4, R₇ is a group

R₈ is C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₃-C₂₀alkyl which is interrupted byone or more O, N or S and/or substituted by OH, C₁-C₄alkyl which issubstituted by —P(O)(OR₁₄)₂, —N(R₉)(R₁₀) or —OCOR₁₁ and/or OH,C₃-C₁₈alkenyl, glycidyl or C₇-C₁₁phenylalkyl,

R₉ and R₁₀ independently of one another are C₁-C₁₂alkyl,C₃-C₁₂alkoxyalkyl, C₄-C₁₆dialkylaminoalkyl or C₅-C₁₂cycloalkyl, or R₉and R₁₀ together are C₃-C₉alkylene or C₃-C₉oxaalkylene orC₃-C₉azaalkylene,

R₁₁ is C₁-C₁₈alkyl, C₂-C₁₈alkenyl or phenyl,

R₁₂ is C₁-C₁₈alkyl, C₂-C₁₈alkenyl, phenyl, C₁-C₁₂alkoxy, phenoxy,C₁-C₁₂alkylamino or C₆-C₁₂arylamino or a group —R₂₄—COOH or —NH—R₁₇—NCO,

R₁₃ is C₁-C₁₂alkyl, C₆-C₁₂aryl or C₇-C₁₄alkaryl,

R₁₄ is C₁-C₁₂alkyl or phenyl,

R₁₅ is C₂-C₁₀alkylene, C₄-C₅₀alkylene which is interrupted by one ormore O, phenylene or a group -phenylene-X-phenylene- in which X is —O—,—S—, —SO₂—, —CH₂— or —C(CH₃)₂—,

R₁₆ is C₂-C₁₀alkylene, C₂-C₁₀oxaalkylene or C₂-C₁₀thiaalkylene,C₆-C₁₂arylene or C₂-C₆alkenylene,

R₁₇ is C₂-C₁₀alkylene, phenylene, tolylene, diphenylenemethane or agroup

R₁₈ is C₂-C₁₀alkylene or C₄-C₂₀alkylene which is interrupted by one ormore O,

R₁₉ is C₃-C₁₂alkanetriyl,

R₂₀ is C₄-C₁₂alkanetetryl,

R₂₃ is C₂-C₁₀alkylene, phenylene or a group

 wherein X is O, S, SO₂, CH₂ or C(CH₃)₂, and

R₂₄ is C₂-C₁₄alkylene, vinylene or o-phenylene.

If one of the substituents in formula I is C₁-C₁₂alkyl, it can beunbranched or branched alkyl, for example methyl, ethyl, propyl,isopropyl, n-butyl, i-butyl, s-butyl or t-butyl, pentyl, hexyl, heptyl,octyl, 2-ethylhexyl, di-t-octyl, nonyl, decyl, undecyl or dodecyl. AsC₁-C₁₈alkyl, R₈, R₁₁ and R₁₂ can additionally be, for example,tetradecyl, hexadecyl or octadecyl.

As C₁-C₁₈alkoxy, R₃ and R₄ are preferably C₁-C₁₂alkoxy. The alkoxyradical is preferably unbranched. Examples of these are methoxy, ethoxy,propoxy, butoxy, hexyloxy, octyloxy, decyloxy or dodecyloxy.

As substituted C₁-C₁₂alkyl, R₇ can be substituted by one or more of thegroups OH, C₁-C₁₈alkoxy, halogen, phenoxy which is unsubstituted orsubstituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen, —COOH, —COOR₈,—CONII₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, —NHR₉, —NH(R₉)(R₁₀), —NHCOR₁₁,—CN or —OCOR₁₁. The following groups are examples of such substitutedalkyl groups: —CH₂CH₂OH, —CH₂CH(OH)CH₃, —CH₂CH(OH)C₂H₅, —CH₂CH(OH)C₆H₁₃,—CH₂CH(OH)C₁₀H₂₁, —CH₂CH₂OCH₃, —CH₂CH₂OC₂H₅, —CH₂CH₂OC₄H₉, —(CH₂)₃OH,—CH₂CH(OH)CH₂OC₄H₉, —CH₂CH(OH)CH₂OC₁₂H₂₅, —CH₂CH₂Ophenyl, —CH₂CH₂Cl,—CH₂CH(OH)CH₂Ophenyl,

—CH₂COOH, —CH₂CH₂COOH, —CH₂COOC₂H₅, —CH₂COOC₈H₁₇, —CH₂CH₂COOCH₃,—CH₂CH₂COOC₄H₉, —CH₂CH₂COOC₁₂H₂₅, —CH₂CONH₂, —CH₂CONHC₄H₉,—CH₂CON(C₄H₉)₂, —CH₂CH₂CONHC₁₂H₂₅, —CH₂CH₂CON(C₂H₅)₂, —CH₂CH₂NH₂,—CH₂CH₂N(CH₃)₂, —(CH₂)₃—NH₂, —(CH₂)₃—NHC₄H₉, —(CH₂)₃N(CH₃)₂,—(CH₂)₃N(C₂H₅)₂, —(CH₂)₃NHCOCH₃, —(CH₂)₃NHCOC₇H₁₅, —CH₂CH₂CN,—CH₂CH₂OCOC₃H₇, —CH₂CH₂OCOC₁₇H₃₅, —CH₂CH(CH₃)—OCOCH₃,—CH₂CH(OCOCH₃)CH₂OC₈H₁₇ or —CH₂CH(OCOC₇H₁₅)CH₂Ophenyl.

As C₃-C₆alkenyl, R₇ can, for example, be allyl, methallyl or 2-butenyl.As C₃-C₁₈alkenyl, R₈ can additionally also be, for example, octenyl,dodecenyl or oleyl. As C₂-C₁₈alkenyl, R₁₁ and R₁₂ can additionally alsobe vinyl.

As C₇-C₁₁phenylalkyl which is unsubstituted or substituted by OH, Cl orCH₃, R₇ and R₈ can, for example, be phenylethyl,2-hydroxy-2-phenylethyl, 2-phenylpropyl, 3-phenylpropyl, 4-chlorobenzylor 4-methylbenzyl, but especially benzyl.

As C₂-C₁₆alkylene, R₇ can be unbranched or branched alkylene, forexample di-, tri-, tetra-, hexa-, octa-, deca- or dodeca-methylene,2,2-dimethyl-prop-1,3-ylene or 1,2-propylene. As C₄-C₁₂alkenylene, R₇can, in particular, be 2-buten-1,4-ylene. As C₃-C₂₀alkylene which isinterrupted by O and/or substituted by OH, R₇ can, for example, be oneof the groups —CH₂CH(OH)CH₂—, —CH₂CH₂OCH₂CH₂— or—CH₂CH(OH)CH₂O—(CH₂)_(x)—OCH₂CH(OH)CH₂— in which x=2-10.

As C₃-C₂₀alkyl which is interrupted and/or substituted by OH, R₈ can, inparticular, be alkyl which is substituted by OH or alkyl which isinterrupted by O and substituted by OH. Examples of these are the groups—CH₂CH₂OH, —CH₂CH(OH)CH₃, —CH₂CH(OH)C₆H₁₃, —CH₂CH₂OC₄H₉,—CH₂CH₂OCH₂CH₂OH or —CH₂CH₂(OCH₂CH₂)_(p)OH in which p=2-9.

As C₁-C₄alkyl which is substituted by —P(O)(OR₁₄)₂, —N(R₉)(R₁₀) or—OCOR₁₁, R₈ can, for example, be —CH₂CH₂P(O)(OC₂H₅)₂, —CH₂P(O)(OC₆H₁₃)₂,—CH₂CH₂N(CH₃)₂, —CH₂CH₂CH₂N(C₂H₅)₂, —CH₂CH₂OCOC₇H₁₅ or —CH₂CH₂OCOCH═CH₂.

As C₃-C₁₂alkoxyalkyl, R₉ and R₁₀ can, in particular, be2-(C₁-C₁₀alkoxy)-ethyl, for example 2-methoxyethyl, 2-butoxyethyl or2-octyloxyethyl. As C₄-C₁₆dialkylaminoalkyl, R₉ and R₁₀ can, forexample, be 2-dibutylaminoethyl, 2-diethylaminoethyl or3-dimethylaminopropyl.

As C₅-C₁₂cycloalkyl, R₉ and R₁₀ can, for example, be cyclopentyl,cyclooctyl or cyclododecyl, but especially cyclohexyl. If R₉ and R₁₀together are C₃-C₉alkylene, C₃-C₉oxaalkylene or C₃-C₉azaalkylene, theyform, together with the N atom to which they are attached, aheterocyclic ring, for example a pyrrolidine, piperidine,2,6-dimethylpiperidine, morpholine, dimethylmorpholine or piperazinering.

As C₁-C₁₂alkoxy, R₁₂ can, for example, be methoxy, ethoxy, butoxy,hexyloxy, octyloxy, decyloxy or dodecyloxy.

As C₁-C₁₂alkylamino or C₆-C₁₂arylamino, R₁₂ can, for example, behexylamino, dodecylamino, phenylamino, naphthylamino or biphenylylamino.

As C₂-C₁₀alkylene, R₁₆, R₁₇ and R₁₈ can be unbranched or branchedalkylene, for example 1,2-ethylene, tri-, tetra-, penta-, hexa-, octa-or deca-methylene, 1,2-propylene or 2,2-dimethyltrimethylene, while asoxaalkylene or thiaalkylene, R₁₆ can, for example, be 2-oxatrimethylene,3-oxapentamethylene, 3-thiapentamethylene or 2-thiatrimethylene. AsC₂-C₆alkenylene, R₁₆ can, in particular, be —CH═CH—.

As C₆-C₁₂arylene, R₁₆ and R₁₇ can, for example, be phenylene,naphthylene or biphenylene. As C₇-C₁₅alkylarylene, R₁₇ can, inparticular, be tolylene.

As C₄-C₂₀alkylene which is interrupted by O, R₁₈ can be interrupted by1-9 O atoms and can, in particular, be the divalent radical formed byremoving the two hydroxyl groups from a polyethylene glycol orpolypropylene glycol.

In the substituents, aryl on its own or in combined radicals ispreferably phenyl, naphthyl or biphenylyl.

Compounds of the formula I which are preferred as the component (b) arethose in which n is 1 to 4, R₁ and R₂ independently of one another areH, OH or C₁-C₄alkyl, R₃ and R₄ independently of one another are H, OH,C₁-C₄alkyl, C₁-C₄alkoxy, halogen or a radical —OR₇, R₅ and R₆independently of one another are H or C₁-C₄akyl, R₇, if n is 1, is a)C₁-C₁₈alkyl which is substituted by one or more of the groups OH,C₁-C₁₈alkoxy, allyloxy, phenoxy, furyloxy,

—COOR₈, —CON(R₉)(R₁₀) and/or by —OCOR₁₁,

b) C₄-C₅₀alkyl which is interrupted by one or more O and can besubstituted by OH or/and glycidyloxy,

c) allyl, glycidyl or benzyl,

d) cyclohexyl or hydroxycyclohexyl,

 and if n is 2, R₇ is C₄-C₁₂alkenylene, C₄-C₆alkenylene, xylylene,C₃-C₂₀alkylene which is interrupted by one or more O and/or substitutedby OH, or R₇ is a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—,—CH₂—COO—R₁₈—OOC—CH₂— or

 and if n is 3, R₇ is a group

 and if n is 4, R₇ is a group

R₈ is C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₃-C₂₀alkyl which is interrupted byone or more O and/or substituted by OH or R₈ is C₁-C₄alkyl which issubstituted by —P(O)(OR₁₄)₂,

R₉ and R₁₀ are C₁-C₆alkyl or R₉ and R₁₀ together are pentamethylene or3-oxapentamethylene,

R₁₁ is C₁-C₁₂alkyl, C₂-C₅alkenyl or phenyl,

R₁₄ is C₁-C₁₄alkyl,

R₁₅ is C₂-C₈alkylene, C₄-C₅₀alkylene which is interrupted by one or moreO, or is a group

R₁₆ is C₂-C₈alkylene, C₂-C₆oxaalkylene or C₂-C₆thiaalkylene and R₁₈ isC₄-C₈alkylene or C₄-C₁₂alkylene which is interrupted by one or more O.

R₁ and R₂ are preferably hydrogen, chlorine or C₁-C₄alkyl, particularlyhydrogen or methyl. R₃ and R₄ are preferably hydrogen, chlorine orC₁-C₄alkyl, particularly hydrogen, chlorine or methyl. R₅ and R₆ arepreferably hydrogen.

Compounds of the formula I which are particularly preferred as component(b) are those in which n is 1, 2 or 4, R₁ and R₂ independently of oneanother are H or CH₃, R₃ and R₄ independently of one another are H, CH₃or Cl, R₅ and R₆ are hydrogen, R₇, if n is 1, is a) C₁-C₁₄alkyl which issubstituted by one or more of the groups OH, C₁-C₁₅alkoxy, allyloxy,phenoxy, furyloxy,

—COOR₈, —CON(R₉)(R₁₀) and/or by —OCOR₁₁,

b) C₆-C₄₅alkyl which is interrupted by one or more O and can besubstituted by OH or/and glycidyloxy,

c) glycidyl or

d) hydroxycyclohexyl,

 and if n is 2, R₇ is C₆-C₁₂alkenylene, 2-butenylene-1,4, xylylene,C₃-C₂₀alkylene which is interrupted by one or more O or substituted byOH, or R₇ is a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—,—CH₂—COO—R₁₈—OOC—CH₂— or

 and if n is 4, R₇ is

R₈ is C₄-C₁₀alkyl, oleyl, C₃-C₂₀alkyl which is interrupted by one ormore O and/or substituted by OH, or R₈ is —CH₂P(O)(OR₁₄)₂,

R₉ and R₁₀ are C₂-C₆alkyl

R₁₁ is C₆-C₁₀alkyl, C₂-C₃alkenyl

R₁₄ is C₁-C₁₄alkyl,

R₁₅ is C₂-C₈alkylene, C₁₀-C₄₅alkylene which is interrupted by more thanone O, or is a group

R₁₆ is C₄-C₈alkylene and R₁₈ is C₄-C₈alkylene.

A further preferred group of compounds of the formula I is formed bythose in which n is 1 or 2 and, if n is 1, R₇ is a group—CH₂CH(OH)CH₂—OR₂₁ in which R₂₁ is C₁-C₁₈alkyl, allyl, phenyl, furyl,C₆-C₁₂-alkanoyl or C₃-C₅alkenoyl and, if n is 2, R₇ is a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂— in which R₁₅ is as defined above.

The following compounds are examples of individual compounds of theformula I

R₇=CH₂ phenyl

—CH₂CH₂OH

—CH₂CH₂OCOCH₃

—CH₂CH₂OCOCH═CH₂

—CH₂CH(OH)CH₂OC₈H₁₇

—CH₂CH(OH)CH₂O(CH₂)₁₂₋₁₄CH₃

—CH₂CH(OH)CH₂O phenyl

—CH₂CH(OH)CH₂OCOC(CH₃)═CH₂

—CH₂COOH

—CH₂CH₂COOC₄H₉

—CH₂COOC₈H₁₇

—CH₂COO(CH₂CH₂O)₇H

—CH₂COOCH₂CH(OH)CH₂OCOCH═CH₂

—CH₂COOCH₂CH(CH₃)OCH₂CH(CH₃)OCH(CH₃)CH₃

—CH₂COOCH₂P(O)(OC₂H₅)₂

—CH₂COOCH₂CH(OH)CH₂P(O)(OC₄H₉)₂

—CH₂COO(CH₂)₇CH═CHC₈H₁₇

—CH₂COOCH₂CH₂OCH₂CH₂OC₆H₁₃

—CH₂CON(C₂H₅)₂

—CH₂CONHCH₂CH₂CH₂N(CH₃)₂

—CH₂CONHC₈H₁₇

—CH₂CON(C₈H₁₇)₂

R₇=—CH₂COOC₂H₅

—CH₂COOCH₂CH₂OCH₃

—CH₂COOCH₂CH═CH-phenyl

—CH₂CH(OH)CH₂O(CH₂)₁₂₋₁₄CH₃

—CH₂COOCH₂CH(OH)CH₂OC₈H₁₇

—CH₂phenyl

—CH₂CH═CH₂

—CH₂CON(C₄H₉)₂

—CH₂CH₂CONHC₈H₁₇

—CO—OC₆H₁₃

—CH₂CH₂Cl

—CH₂CH₂CN

R₇=—CH₂CH(OH)phenyl

—CH₂CH(OH)CH₂O(CH₂)₁₂₋₁₄CH₃

—CH₂CH(OH)CH₂OCOphenyl

—CH₂CH(CH₃)OCOCH₃

—SO₂—C₁₂H₁₅

—CH₂COOC₁₀H₂₁

—CH₂CONHCH₂CH₂OCH₃

—CH₂CH₂CONHCH₂phenyl

—(CH₂)₃CONH(CH₂)₃N(C₂H₅)₂

CH₂CONHC₁₂H₂₅

R₇=—CH₂CH(OH)CH₂—

—CH₂—CH═CH—CH₂—

—(CH₂)₄—

—(CH₂)₆—

—(CH₂)₈

—(CH₂)₁₂—

—CH₂CH(OH)CH₂O—CH₂CH₂—OCH₂CH(OH)CH₂—

—CH₂CH(OH)CH₂O—(CH₂)₆—OCH₂CH(OH)CH₂—

—CH₂COO—(CH₂)₆—OCOCH₂—

—CO—(CH₂)₈—CO—

R₇=—CH₂CH(OH)CH₃

—CH₂CH₂OC₄H₉

—CH₂CH₂COC₂H₅

—CH₂COOC₈H₁₇

—CH₂CH(OH)CH₂OC₄H₉

—CH₂CH(OH)CH₂Ophenyl

R₇=—CH₂CH₂OH

—CH₂CH₂Ophenyl

—CH₂COOC₆H₁₃

—CH₂CH₂COO(CH₂CH₂O)₃H

—CH₂CH(OH)CH₂OC₆H₁₃

—CH₂CH(OH)CH₂phenyl

Some of the triazine derivatives of the formula I are known compounds.Many such compounds and also their preparation and their use as UVabsorbers for organic materials are described in U.S. Pat. Nos.3,244,708, 3,249,608 and 3,423,360. Their use in photographic materialsis described in U.S. Pat. No. 3,843,371.

Another fraction of the triazine derivatives constitutes novelcompounds. Compounds which are novel and are also a subject of thepresent invention are those of the formula Ia

in which n is 1 to 4,

R₁ and R₂ independently of one another are H, OH, C₁-C₁₂alkyl,cyclohexyl or trifluoromethyl,

R₃ and R₄ independently of one another are H, OH, C₁-C₁₂alkyl,cyclohexyl, C₁-C₁₈alkoxy or halogen and, in the event that n=1, can alsobe a radical —OR₇,

R₅ and R₆ independently of one another are H, C₁-C₁₂alkyl or halogen,

R₇, if n is 1, is a) C₁-C₁₂alkyl which is substituted by phenoxy (whichis unsubstituted or substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen)or by a group —COOR₈, —CONH₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, NHR₉,—N(R₉)(R₁₀) or —O—CO—R₂₂,

b) C₄-C₅₀alkyl which is interrupted by more than one O and can besubstituted by OH or/and glycidyloxy, be substituted by OH or/andglycidyloxy,

c) glycidyl or a group

d) cyclohexyl substituted by OH or —OCOR₁₁

e) a group —CH₂CH(OH)CH₂OR₂₁

f) a group —SO₂—R₁₃,

g) a group —CO—R₁₂,

 and if n is 2, R₇ is

a) C₂-C₁₂alkylene,

b) C₄-C₁₂alkenylene,

c) xylylene,

d) C₃-C₂₀alkylene which is interrupted by one or more O and/orsubstituted by OH,

e) a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—,—(CH₂)_(m)—COO—R₁₈—OOC—(CH₂)_(m)— (wherein m is 1-3) or

 and if n is 3, R₇ is a group

 (wherein m is 1-3),

 and if n is 4, R₇ is a group

 (wherein m is 1-3),

R₈ is C₃-C₂₀alkyl which is interrupted by one or more O, N or S and canbe substituted by OH, or R₈ is C₁-C₄alkyl which is substituted by—P(O)(OR₁₄)₂, —N(R₉)(R₁₀), or —OCOR₁₁ and/or OH, or R₈ is C₃-C₁₈alkenyl,glycidyl or C₇-C₁₁phenylalkyl,

R₉ and R₁₀ independently are C₁-C₁₂alkyl, C₃-C₁₂alkoxyalkyl,C₄-C₁₆dialkylaminoalkyl or C₅-C₁₂cycloalkyl, or R₉ and R₁₀ together areC₃-C₉alkylene or C₃-C₉oxaalkylene or C₃-C₉azalkylene,

R₁₁ is C₁-C₁₈alkyl, C₂-C₁₈alkenyl or phenyl,

R₁₂ is a group —R₂₄—COOH or —NH—R₁₇—NCO,

R₁₃ is C₁-C₁₂alkyl, C₆-C₁₂aryl or C₇-C₁₄alkaryl

R₁₄ is C₁-C₁₂ alkyl or phenyl

R₁₅ is C₂-C₁₀alkylene, C₄-C₅₀alkylene which is interrupted by one ormore O, or R₁₅ is phenylene or a group -phenylene-X-phenylene- in whichX is —O—, —S—, —SO₂—, —CH₂— or —C(CH₃)₂—,

R₁₇ is C₂-C₁₀alkylene, phenylene, tolylene, diphenylenemethane or agroup

R₁₈ is C₂-C₁₀alkylene or C₄-C₂₀alkylene which is interrupted by one ormore O,

R₁₉ is C₃-C₁₂alkanetriyl,

R₂₀ is C₄-C₁₂alkanetetryl,

R₂₁ is H, C₁-C₁₈alkyl, C₃-C₁₈alkenyl, phenyl, phenyl substituted byC₁-C₁₂alkyl, C₁-C₂alkoxy or halogen, or R₂₁ is C₂-C₁₉alkanoyl, benzoyl,C₃-C₁₈alkenoyl, furyl or a group

R₂₂ is C₂-C₅alkenyl,

R₂₃ is C₂-C₁₀alkylene, phenylene or a group

 wherein X is O, S, SO₂, CH₂ or C(CH₃)₂, and

R₂₄ is C₂-C₁₄alkylene, vinylene or o-phenylene.

Amongst these compounds of the formula Ia, preferred compounds are thosein which n is 1 to 4, R₁ and R₂ independently of one another are H, OHor C₁-C₄alkyl, R₃ and R₄ independently of one another are H, OH,C₁-C₄alkyl, C₁-C₄alkoxy, halogen or a radical —OR₇, R₅ and R₆independently of one another are H or C₁-C₄alkyl, R₇, if n is 1, isC₁-C₆alkyl which is substituted by —COOR₈, —COONHR₉, —CON(R₉)(R₁₀) or—OCOR₂₂, or R₇ is glycidyl, hydroxycyclohexyl or a group—CH₂CH(OH)CH₂OR₂₁, and if n is 2, R₇ is C₄-C₁₂alkylene, C₄-C₆alkenylene,xylylene, C₃-C₂₀alkylene which is interrupted by one or more O and/orsubstituted by OH, or R₇ is a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—,—CH₂—COO—R₁₈—OOCCH₂— or

and if n is 3, R₇ is a group

and if n is 4, R₇ is a group

R₈ is C₃-C₂₀alkyl which is interrupted by one or more O and can besubstituted by OH or

R₈ is C₁-C₄alkyl which is substituted by —P(O)(OR₁₄)₂ or R₈ isC₃-C₁₈alkenyl,

R₉ and R₁₀ independently are C₁-C₈alkyl or cyclohexyl or R₉ and R₁₀together are pentamethylene or 3-oxapentamethylene,

R₁₄ is C₁-C₁₄alkyl,

R₁₅ is C₂-C₈alkylene, C₄-C₅₀alkylene which is interrupted by one or moreO, or R₁₅ is a group -phenylene-X-phenylene- in which X is —O—, —CH₂— or—C(CH₃)₂—,

R₁₈ is C₄-C₈alkylene or C₄-C₁₂alkylene which is interrupted by one ormore O,

R₂₁ is H, C₄-C₁₈alkyl, allyl, phenyl, furyl, C₅-C₁₉alkanoyl orC₃-C₅alkenoyl and R₂₂ is C₂-C₅alkenyl, in particular those in which n is1, 2 or 4, R₁ and R₂ independently of one another are H or CH₃, R₃ andR₄ independently of one another are H, CH₃ or Cl, R₅ and R₆ arehydrogen,

R₇, if n is 1, is C₁-C₄alkyl which is substituted by —COOR₈,—CON(R₉)(R₁₀) or —O—COR₂₂, or R₇ is glycidyl, 2-hydroxycyclohexyl or agroup —CH₂CH(OH)CH₂OR₂₁,

 and if n is 2, R₇ is C₆-C₁₂alkenylene, 2-butene-1,4-ylene, xylylene orC₃-C₂₀alkylene which is interrupted by one or more O and/or substitutedby OH, or R₇ is a group —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—,—CH₂—COO—R₁₈—OOCCH₂— or

 and if n is 4, R₇ is a group

R₈ is C₃-C₂₀alkyl which is interrupted by one or more O and can besubstituted by OH or

R₈ is —CH₂P(O)(OR₁₄)₂ or oleyl

R₉ and R₁₀ are C₂-C₆alkyl

R₁₅ is C₂-C₈alkylene, C₁₀-C₄₅alkylene which is interrupted by one ormore O or is a group

R₁₈ is C₄-C₈alkylene,

R₂₁ is H, C₄-C₁₅alkyl, allyl, phenyl, furyl, C₅-C₁₂alkanoyl orC₃-C₅alkenoyl and R₂₂ is C₂-C₃alkenyl.

The compounds of the formula Ia in which n is 2 are also preferred.

In general, the compounds of the formula I and Ia can be prepared byintroducing the radical R₇ into the p-hydroxyl group in a compound ofthe formula II

The compounds of the formula II are known compounds and can be preparedby a Friedel-Crafts reaction between cyanuric chloride and 1 mole of anaromatic compound of the formula

and 1 mole of an aromatic compound of the formula

and 1 mole of resorcinol, as described, for example, in Swiss Patent480,091 or in Swiss Patent 484,695 or in U.S. Pat. No. 3,244,708.

The conversion of II into I can be effected by various processes knownper se, depending on the nature of the radical R₇. If R₇ is substitutedalkyl, alkenyl, glycidyl, phenylalkyl, —CO—R₁₂, —SO₂—R₁₃, alkylene,alkenylene, xylylene or —COR₁₆CO—, the compound II or an alkali metalsalt thereof can be reacted with a halogen compound of the formulaHal-R₇ or Hal-R₇-Hal in which Hal is chlorine, bromine or iodine, inparticular with the compounds Cl—R₇ and Cl—R₇—Cl.

If R₇ is a group

in which R′ is hydrogen or CH₃ and Y is —COOR₈, —CONH₂, —CONHR₉,—CON(R₉)(R₁₀) or —CN, the compounds can be prepared by reacting acompound of the formula II with a compound of the formula

in the manner of a so-called Michael addition reaction.

If R₇ is a group —CH₂CH(OH)—W in which W is alkyl, phenyl, phenylalkylor —CH₂OR₂₁, such compounds can be prepared by reacting a compound ofthe formula II with an epoxide of the formula

Analogously, compounds of the formula I in which n is 2 and R₇ is agroup —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, can be prepared by reacting 2moles of a compound II and 1 mole of a bis-glycidyl ether of the formula

Compounds of the formula I in which R₇ is cyclohexyl substituted by OHcan be prepared by reaction of II with cyclohexene oxide.

Compounds of the formula I in which n is 2 and R₇ is —CO—NH—R₁₇—NH—CO—can be prepared by reacting 2 moles of a compound of the formula II withI mole of a diisocyanate OCN—R₁₇—NCO. Compounds of the formula I inwhich n is 2 and R₇ is a group —CH₂CH(OH)CH₂— can be prepared byreacting 2 moles of a compound II with 1 mole of epichlorohydrin.

Compounds of formula I or Ia wherein n is 1 and R₇ is a group

or a group —CO—R₂₄—COOH or —CONH—R₁₇—NCO can be prepared from II byreaction with one molar equivalent of a compound R₂₃

or OCN—R₁₇—NCO respectively.

It is also possible to convert a compound of the formula I into anothercompound of the formula I. For example, a hydroxyalkyl or aminoalkylradical R₇ can be converted by acylation with R₁₁COCl into thecorresponding acyloxy or acylamino derivative.

Or a cyanoalkyl radical R₇ can be converted by reduction into anaminoalkyl radical. Compounds in which R₇ is alkyl which is substitutedby —COOR₈ can be transesterified with another alcohol or polyol.

The methods required for the individual stages of the synthesis areknown to those skilled in the art; some of them are described in greaterdetail in the examples which follow later.

The polyalkylpiperidines used as the component (a) preferably contain atleast one group of the formula

in which R is hydrogen or methyl. R is preferably hydrogen. These arederivatives of polyalkylpiperidines, in particular of2,2,6,6-tetramethylpiperidine. These compounds preferably carry one ortwo polar substituents or a polar spiro ring system in the 4-position ofthe piperidine ring. These compounds can be low-molecular or oligomericor polymeric compounds.

The following classes of polyalkylpiperidines are of particularimportance.

a) Compounds of the formula III

 in which n is a number from 1 to 4, R is hydrogen or methyl, R₃₁ ishydrogen, amine oxide, hydroxyl, C₁-C₁₂alkyl, C₃-C₈alkenyl,C₃-C₈alkinyl, C₇-C₁₂aralkyl, C₁-C₁₈alkoxy, C₅-C₈cycloalkoxy,C₇-C₉phenylalkoxy, C₁-C₈alkanoyl, C₃-C₅alkenoyl, C₁-C₁₈alkanoyloxy,benzyloxy, glycidyl or a group —CH₂CH(OH)—Z, in which Z is hydrogen,methyl or phenyl, R₃₁ being preferably H, C₁-C₄alkyl, allyl, benzyl,acetyl or acryloyl, and, if n is 1, R₃₂ is hydrogen, C₁-C₁₈alkyl whichcan be interrupted by one or more oxygen atoms, cyanoethyl, benzyl,glycidyl, a monovalent radical of an aliphatic, cycloaliphatic,araliphatic, unsaturated or aromatic carboxylic acid, carbamic acid oran acid containing phosphorus or a monovalent silyl radical, preferablya radical of an aliphatic carboxylic acid having 2 to 18 C atoms, acycloaliphatic carboxylic acid having 7 to 15 C atoms, anα,β-unsaturated carboxylic acid having 3 to 5 C atoms or an aromaticcarboxylic acid having 7 to 15 C atoms, or, if n is 2, isC₁-C₁₂alkylene, C₄-C₁₂alkenylene, xylylene, a divalent radical of analiphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid,dicarbamic acid, or acid containing phosphorus, or a divalent silylradical, preferably a radical of an aliphatic dicarboxylic acid having 2to 36 C atoms, a cycloaliphatic or aromatic dicarboxylic acid having8-14 C atoms or an aliphatic, cycloaliphatic or aromatic dicarbamic acidhaving 8-14 C atoms, or, if n is 3, is a trivalent radical of analiphatic, cycloaliphatic or aromatic tricarboxylic acid, an aromatictricarbamic acid or an acid containing phosphorus, or a trivalent silylradical, and, if n is 4, is a tetravalent radical of an aliphatic,cycloaliphatic or aromatic tetracarboxylic acid.

Examples of possible C₁-C₁₂alkyl substituents are methyl, ethyl,n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl,2-ethylhexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.

As C₁-C₁₈alkyl, R₃₁ or R₃₂ can be the groups defined above andadditionally, for example, n-tridecyl, n-tetradecyl, n-hexadecyl orn-octadecyl.

As C₃-C₈alkenyl, R₃₁ can, for example, be 1-propenyl, allyl, methallyl,2-butenyl, 2-pentenyl, 2-hexenyl, 2-octenyl, 4-tert-butyl-2-butenyl.

As C₃-C₈alkinyl, R₃₁ is preferably propargyl.

As C₇-C₁₂aralkyl, R₃₁ is especially phenethyl and, in particular,benzyl.

Examples of R₃₁ as C₁-C₈alkanoyl are formyl, propionyl, butyryl oroctanoyl, but preferably acetyl, and examples of R₂₁ as C₃-C₅alkenoylare especially acryloyl.

Examples of R₃₁ as C₁-C₁₈alkoxy are hexyloxy, heptyloxy, octyloxy ordecyloxy. As cycloalkoxy, R₃₁ is preferably cyclohexyloxy. Asphenylalkoxy, R₃₁ is preferably benzyloxy. Examples of R₃₁ asalkanoyloxy are acetoxy, butyroyloxy, hexanoyloxy, octanoyloxy,decanoyloxy or stearoyloxy.

Examples of R₃₂ as a monovalent radical of a carboxylic acid are aradical of acetic acid, caproic acid, stearic acid, acrylic acid,methacrylic acid, benzoic acid orβ-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid.

Examples of R₃₂ as a divalent radical of a dicarboxylic acid are aradical of malonic acid, succinic acid, glutaric acid, adipic acid,suberic acid, sebacic acid, maleic acid, itaconic acid, phthalic acid,dibutylmalonic acid, dibenzylmalonic acid,butyl-(3,5-di-tert-butyl-4-hydroxybenzyl)-malonic acid orbicycloheptenedicarboxylic acid.

Examples of R₃₂ as a trivalent radical of a tricarboxylic acid are aradical of trimellitic acid, citric acid or nitrilotriacetic acid.

Examples of R₃₂ as a tetravalent radical of a tetracarboxylic acid arethe tetravalent radical of butane-1,2,3,4-tetracarboxylic acid orpyromellitic acid.

Examples of R₃₂ as a divalent radical of a dicarbamic acid are a radicalof hexamethylenedicarbamic acid or 2,4-toluylenedicarbamic acid.

Preferred compounds of the formula III are those in which R is hydrogen,R₃₁ is hydrogen or methyl, n is 1 and R₃₂ is C₁-C₁₈alkyl, or n is 2 andR₃₂ is the diacyl radical of an aliphatic dicarboxylic acid having 4-12C atoms.

The following compounds are examples of polyalkylpiperidine compounds ofthis class:

1) 4-Hydroxy-2,2,6,6-tetramethylpiperidine,

2) 1-Allyl-4-hydroxy-2,2,6,6-tetramethylpiperidine,

3) 1-Benzyl-4-hydroxy-2,2,6,6-tetramethylpiperidine,

4) 1-(4-tert-Butyl-2-butenyl)₄-hydroxy-2,2,6,6-tetramethylpiperidine,

5) 4-Stearoyloxy-2,2,6,6-tetramethylpiperidine,

6) 1-Ethyl-4-salicyloyloxy-2,2,6,6-tetramethylpiperidine,

7) 4-Methacryloyloxy-1,2,2,6,6-pentamethylpiperidine,

8) 1,2,2,6,6-Pentamethylpiperidin-4-ylβ-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate,

9) Di-(1-benzyl-2,2,6,6tetramethylpiperidin-4-yl)maleinate,

10) Di-(2,2,6,6-tetramethylpiperidin-4-yl)succinate,

11) Di-(2,2,6,6-tetamethylpiperidin-4-yl)glutarate,

12) Di-(2,2,6,6-tetramethylpiperidin-4-yl)adipate,

13) Di-(2,2,6,6-tetramethylpiperidin-4-yl)sebacate,

14) Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)sebacate,

15) Di-(1,2,3,6-tetramethyl-2,6-diethyl-piperidin-4-yl)sebacate,

16) Di-(1-allyl-2,2,6,6-tetramethylpiperidin-4-yl)phthalate,

17) 1-Hydroxy-4-β-cyanoethyloxy-2,2,6,6-tetramethylpiperidine,

18) 1-Acetyl-2,2,6,6-tetramethylpiperidin-4-yl acetate,

19) Tri-(2,2,6,6-tetramethylpiperidin-4-yl)trimellitate,

20) 1-Acryloyl-4-benzyloxy-2,2,6,6-tetramethylpiperidine,

21) Di-(2,2,6,6-tetamethylpiperidin-4-yl)diethylmalonate,

22) Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)dibutylmalonate,

23)Di-(1,2,2,6,6-pentamethylpiperidin-4-yl)butyl-(3,5-di-tert-butyl-4-hydroxybenzyl)-malonate,

24) Di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate,

25) Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate,

26)Hexane-1′,6′-bis-(4-carbamoyloxy-1-n-butyl-2,2,6,6-tetramethylpiperidine),

27)Toluene-2′,4′-bis-(4-carbamoyloxy-1-n-propyl-2,2,6,6-tetramethylpiperidine),

28) Tetra-(2,2,6,6-tetramethylpiperidin-4-yl)butane-1,2,3,4-tetracarboxylate,

29) Tetra-(1,2,2,6,6-pentamethylpiperidin-4-yl)butane-1,2,3,4-tetracarboxylate,

30) Tris-(1-propyl-2,2,6,6-tetramethylpiperidin-4-yl)phosphite,

31) Tris-(1-propyl-2,2,6,6-tetramethylpiperidin-4-yl)phosphate,

32) Phenyl-[bis-(1,2,2,6,6-pentamethylpiperidin-4-yl)]phosphonate,

33) 4-Hydroxy-1,2,2,6,6-pentamethylpiperidine,

34) 4-Hydroxy-N-hydroxyethyl-2,2,6,6-tetramethylpiperidine,

35) 4-Hydroxy-N-(2-hydroxypropyl)-2,2,6,6-tetramethylpiperidine,

36) 1-Glycidyl-4-hydroxy-2,2,6,6-tetramethylpiperidine.

b) Compounds of the formula IV

 in which n is the number 1 or 2, R and R₃₁ are as defined under a), R₃₃is hydrogen, C₁-C₁₂alkyl, C₂-C₅hydroxyalkyl, C₅-C₇cycloalkyl,C₇-C₈aralkyl, C₂-C₁₈alkanoyl, C₃-C₅alkenoyl, benzoyl or a group of theformula

 and, if n is 1, R₃₄ is hydrogen, C₁-C₁₈alkyl, C₃-C₈alkenyl,C₅-C₇Cycloalkyl, C₁-C₄alkyl which is substituted by a hydroxyl, cyano,alkoxycarbonyl or carbamide group, glycidyl or a group of the formula—CH₂—CH(OH)—Z or of the formula —CONH—Z in which Z is hydrogen, methylor phenyl or R₃₄ is a group —CO—CO—NH—(C₁-C₁₈alkyl); or, if n is 2, R₃₄is C₂-C₁₂alkylene, C₆-C₁₂arylene, xylylene, a —CH₂—CH(OH)—CH₂— group ora group —CH₂—CH(OH)—CH₂—O—D—O— in which D is C₂-C₁₀alkylene,C₆-C₁₅arylene or C₆-C₁₂cycloalkylene or, provided that R₃₃ is notalkanoyl, alkenoyl or benzoyl, R₃₄ can also be a divalent radical of analiphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamicacid or the group —CO—, or, if n is 1, R₃₃ and R₃₄ together can be thedivalent radical of an aliphatic, cycloaliphatic or aromatic1,2-dicarboxylic or 1,3-dicarboxylic acid.

Possible C₁-C₁₂alkyl or C₁-C₁₈alkyl substituents are as already definedunder a).

Possible C₅-C₇cycloalkyl substituents are especially cyclohexyl,

As C₇-C₈aralkyl, R₃₃ is especially phenylethyl or, in particular,benzyl. As C₂-C₅hydroxyalkyl, R₃₃ is especially 2-hydroxyethyl or2-hydroxypropyl.

Examples of R₃₃ as C₂-C₁₈alkanoyl are propionyl, butyryl, octanoyl,dodecanoyl, hexadecanoyl or octadecanoyl, but preferably acetyl, andexamples of R₃₃ as C₃-C₅alkenoyl are especially acryloyl.

Examples of R₃₄ as C₂-C₈alkenyl are allyl, methallyl, 2-butenyl,2-pentenyl, 2-hexenyl or 2-octenyl.

Examples of R₃₄ as C₁-C₄alkyl which is substituted by a hydroxyl, cyano,alkoxycarbonyl or carbamide group are 2-hydroxyethyl, 2-hydroxypropyl,2-cyanoethyl, methoxycarbonylmethyl, 2-ethoxycarbonylethyl,2-aminocarbonylpropyl or 2-(dimethylaminocarbonyl)-ethyl.

Examples of possible C₂-C₁₂alkylene substituents are ethylene,propylene, 2,2-dimethylpropylene, tetamethylene, hexamethylene,octamethylene, decamethylene or dodecamethylene.

Examples of possible C₆-C₁₅arylene substituents are o-, m- orp-phenylene, 1,4-naphthylene or 4,4′-biphenylene.

As C₆-C₁₂cycloalkylene, D is especially cyclohexylene.

Preferred compounds of the formula IV are those in which n is 1 or 2, Ris hydrogen, R₃₁ is hydrogen or methyl, R₃₃ is hydrogen, C₁-C₁₂alkyl ora group of the formula

and, in the event that n=1, R₃₄ is hydrogen or C₁-C₁₂alkyl and, in theevent that n=2, R₃₄ is C₂-C₈alkylene.

The following compounds are examples of polyalkylpiperidine compounds ofthis class:

37)N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylene-1,6-diamine,

38)N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-hexamethylene-1,6-diacetamide,

39) Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-amine,

40) 4-Benzoylamino-2,2,6,6-tetraethylpiperidine,

41) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-N,N′-dibutyladipamide,

42)N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-N,N′-dicyclohexyl-2-hydroxypropylene-1,3-diamine,

43) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-p-xylylenediamine,

44) N,N′-Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-succindiamide,

45) N-(2,2,6,6-Tetramethylpiperidin-4-yl)-β-aminopropionic acid dodecylester,

46) The compound of the formula

47)N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N′-dodecyl-oxalamide

48) N-(2,2,6,6-Tetramethylpiperidin4yl)-α-dodecylsuccinimide,

49) 4-Methacrylamido-1,2,2,6,6-pentamethylpiperidine.

c) Compounds of the formula V,

 in which n is the number 1 or 2, R and R₃₁ are as defined under a) and,if n is 1, R₃₅ is C₂-C₈alkylene or C₂-C₈hydroxyalkylene orC₄-C₂₂acyloxyalkylene and, if n is 2, R₃₅ is the group (—CH₂)₂C(CH₂—)₂.

Examples of R₃₅ as C₂-C₈alkylene or C₂-C₈hydroxyalkylene are ethylene,1-methylethylene, propylene, 2-ethylpropylene or2-ethyl-2-hydroxymethylpropylene.

An example of R₃₅ as C₄-C₂₂acyloxyalkylene is2-ethyl-2-acetoxymethylpropylene.

The following compounds arc examples of polyalkylpiperidine compounds ofthis class:

50) 9-Aza-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecane,

51) 9-Aza-8,8,10,10-tetramethyl-3-ethyl-1,5-dioxaspiro[5.5]undecane,

52) 8-Aza-2,7,7,8,9,9-hexamethyl-1,4dioxaspiro[4.5]decane,

53)9-Aza-3-hydroxymethyl-3-ethyl-8,8,9,10,10-pentamethyl-1,5-dioxaspiro[5.5]undecane,

54)9-Aza-3-ethyl-3-acetoxymethyl-9-acetyl-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecane,

55)2,2,6,6-Tetramethylpiperidin-4-spiro-2′-(1′,3′dioxane)-5′-spiro-5″-(1″,3″-dioxane)-2″-spiro-4′″-(2′″,2′″,6′″,6′″-tetramethylpiperidine).

d) Compounds of the formulae VIA, VIB and VIC

 in which n is the number 1 or 2, R and R₃₁ are as defined under a), R₃₆is hydrogen, C₁-C₁₂alkyl, allyl, benzyl, glycidyl or C₂-C₆alkoxyalkyland, if n is 1, R₃₇ is hydrogen, C₁-C₁₂alkyl, C₃-C₅alkenyl,C₇-C₉aralkyl, C₅-C₇cycloalkyl, C₂-C₄hydroxyalkyl, C₂-C₆alkoxyalkyl,C₆-C₁₀aryl, glycidyl or a group of the formula —(CH₂)_(p)—COO—Q or theformula —(CH₂)_(p)—O—CO—Q in which p is 1 or 2 and Q is C₁-C₄alkyl orphenyl, or, if n is 2, R₃₆ is C₂-C₁₂alkylene, C₄-C₁₂alkenylene,C₆-C₁₂arylene, a group —CH₂—CH(OH)—CH₂—O—D—O—CH₂—CH(OH)—CH₂— in which Dis C₂-C₁₀alkylene, C₆-C₁₅arylene or C₆-C₁₂cycloalkylene, or a group—CH₂CH(OZ′)CH₂—(OCH₂—CH(OZ′)CH₂)₂— in which Z′ is hydrogen, C₁-C₁₈alkyl,allyl, benzyl, C₂-C₁₂alkanoyl or benzoyl, T₁ and T₂ independently of oneanother are hydrogen, C₁-C₁₈alkyl or C₆-C₁₀aryl or C₇-C₉aralkyl each ofwhich is unsubstituted or substituted by halogen or C₁-C₄alkyl, or T₁and T₂, together with the C atom linking them, form a C₅-C₁₂cycloalkanering.

Examples of possible C₁-C₁₂alkyl substituents are methyl, ethyl,n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl,2-ethylhexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.

Examples of possible C₁-C₁₈alkyl substituents can be the groups definedabove and also, for example, n-tridecyl, n-tetradecyl, n-hexadecyl orn-octadecyl.

Examples of possible C₂-C₆alkoxyalkyl substituents are methoxymethyl,ethoxymethyl, propoxymethyl, tert-butoxymethyl, ethoxyethyl,ethoxypropyl, n-butoxyethyl, tert-butoxyethyl, isopropoxyethyl orpropoxypropyl.

Examples of R₃₇ as C₃-C₅alkenyl are 1-propenyl, allyl, methallyl,2-butenyl or 2-pentenyl.

As C₇-C₉aralkyl, R₃₇, T₁ and T₂ are especially phenethyl or, inparticular, benzyl. If T₁ abd T₂, together with the C atom, form acycloalkane ring, this can, for example, be a cyclopentane, cyclohexane,cyclooctane or cyclododecane ring.

Examples of R₃₇ as C₂-C₄hydroxyalkyl are 2-hydroxyethyl,2-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.

As C₆-C₁₀aryl, R₃₇, T₁ and T₂ are especially phenyl, α-naphthyl orβ-naphthyl each of which is unsubstituted or substituted by halogen orC₁-C₄alkyl.

Examples of R₃₇ as C₂-C₁₂alkylene are ethylene, propylene,2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene,decamethylene or dodecamethylene.

As C₄-C₁₂alkenylene, R₃₇ is especially 2-butenylene, 2-pentenylene or3-hexenylene.

Examples of R₃₇ as C₆-C₁₂arylene are o-, m- or p-phenylene,1,4-naphthylene or 4,4′-biphenylene.

Examples of Z′ as C₂-C₁₂alkanoyl are propionyl, butyryl, octanoyl ordodecanoyl, but preferably acetyl.

As C₂-C₁₀alkylene, C₆-C₁₅arylene or C₆-C₁₂cycloalkylene, D is as definedunder b).

The following compounds are examples of polyalkylpiperidine compounds ofthis class:

56) 3-Benzyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione,

57)3-n-Octyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione,

58)3-Allyl-1,3,8-triaza-1,7,7,9,9-pentamethylspiro[4.5]decane-2,4-dione,

59)3-Glycidyl-1,3,8-triaza-7,7,8,9,9-pentamethylspiro[4.5]decane-2,4-dione,

60) 1,3,7,7,8,9,9-Heptamethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,

61)2-Isopropyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane,

62)2,2-Dibutyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane,

63)2,2,4,4-Tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]heneicosane,

64) 2-Butyl-7,7,9,9-tetramethyl-1-oxa-4,8-diaza-3-oxospiro[4.5]decane,

65)8-Acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dioneor the compounds of the following formulae:

e) Compounds of the formula VII,

 in which n is the number 1 or 2 and R₃₃ is a group of the formula

 in which R and R₃₁ are as defined under a), E is —O— or —NR₄₁—, A isC₂-C₆alkylene or —(CH₂)₃—O— and x is the numbers 0 or 1, R₃₉ isidentical with R₃₈ or is one of the groups —NR₄₁R₄₂, —OR₄₃, —NHCH₂OR₄₃or —N(CH₂OR₄₃)₂, R₄₀ is identical with R_(38 or R) ₃₉, if n is 1, and,if n is 2, is a group —E—B—E— in which B is C₂-C₆alkylene which can beinterrupted by —N(R₄₁)—, R₄₁ is C₁-C₁₂alkyl, cyclohexyl, benzyl orC₁-C₄hydroxyalkyl or a group of the formula

R₄₂ is C₁-C₁₂alkyl, cyclohexyl, benzyl or C₁-C₄hydroxyalkyl and R₄₃ ishydrogen, C₁-C₁₂alkyl or phenyl or R₄₁ and R₄₂ together areC₄-C₅alkylene or C₄-C₅oxaalkylene, for example

or R₄₁ and R₄₂ are each a group of the formula

Examples of possible C₁-C₁₂alkyl substituents are methyl, ethyl,n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl,2-ethylhexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.

Examples of possible C₁-C₄hydroxyalkyl substituents are 2-hydroxyethyl,2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.

Examples of A as C₂-C₆alkylene are ethylene, propylene,2,2-dimethylpropylene, tetramethylene or hexamethylene.

Examples of R₄₁ and R₄₂ together as C₄-C₅alkylene or oxaalkylene aretetramethylene, pentamethylene or 3-oxapentamethylene.

The compounds of the following formulae are examples ofpolyalkylpiperidine compounds of this class:

f) Oligomeric or polymeric compounds in which the recurring structuralunit contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (I),in particular polyesters, polyethers, polyamides, polyamines,polyurethanes, polyureas, polyaminotriazines, poly(meth)acrylates,poly(meth)acrylamides and copolymers thereof containing radicals of thistype.

The compounds of the following formulae in which m is a number from 2 toabout 200 are examples of 2,2,6,6-polyalkylpiperidine light stabilizersof this class.

Of these classes of compounds, classes a), d), e) and f) areparticularly suitable, in particular the Compounds Nos. 10, 13, 14, 23,24, 28, 29, 45, 47, 48, 63, 65, 69, 75, 77, 81, 84, 92 and 93.

Examples of organic materials which can be stabilized with the mixtureof (a) and (b) or with a compound of the formula Ia are fats, waxes,oils, cosmetics or photographic materials, but particularly organicpolymers. The following classes are examples of polymers of this type:

1. Polymers of monoolefins and diolefins, for example polypropylene,polyisobutylene, polybut-1-ene, polymethylpent-1-ene, polyisoprene orpolybutadiene, and polymerizates of cycloolefins, for examplecyclopentene or norbornene; and also polyethylene (which can, ifdesired, be crosslinked), for example high-density polyethylene (HDPE),low-density polyethylene (LDPE) and linear low-density polyethylene(LLDPE).

2. Mixtures of the polymers mentioned under 1), for example mixtures ofpolypropylene with polyisobutylene or of polypropylene with polyethylene(for example PP/HDPE or PP/LDPE) and mixtures of different types ofpolyethylene (for example LDPE/HDPE).

3. Copolymers of monoolefins and diolefins with one another or withother vinyl monomers, for example ethylene/propylene copolymers, linearlow-density polyethylene (LLDPE) and mixtures thereof with low-densitypolyethylene (LDPE), propylene/but-1-ene copolymers,propylene/isobutylene copolymers, ethylene/but-1-ene copolymers,ethylene/hexene copolymers, ethylene/methylpentene copolymers,ethylene/heptene copolymers, ethylene/octene copolymers,propylene/butadiene copolymers, isobutylene/isoprene copolymers,ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylatecopolymers, ethylene/vinyl acetate copolymers or ethylene/acrylic acidcopolymers and salts thereof (ionomers), and also terpolymers ofethylene with propylene and a diene, such as hexadiene,dicyclopentadiene or ethylidenenorbornene; and also mixtures of suchcopolymers with one another and with polymers mentioned under 1), forexample polypropylene/ethylene/propylene copolymers, LDPE-ethylene/vinylacetate copolymers, LDPE-ethylene/acrylic acid copolymers,LLDPE-ethylene/vinyl acetate copolymers and LLDPE-ethylene/acrylic acidcopolymers.

3a Hydrocarbon resins (for example C₅-C₉), including hydrogenatedmodifications thereof (for example tackifying resins).

4. Polystyrene, poly-(p-methylstyrene) and poly-(α-methylstyrene).

5. Copolymers of styrene or α-methylstyrene with dienes or acrylicderivatives, for example styrene/butadiene, styrene/acrylonitrile,styrene/alkyl methacrylate, styrene/butadiene/alkyl acrylate,styrene/maleic anhydride or styrene/acrylonitrile/methyl acrylate;mixtures of high impact resistance formed from styrene copolymers andanother polymer, for example a polyacrylate, a diene polymer or anethylene/propylene/diene terpolymer, and block copolymers of styrene,for example styrene/butadiene/styrene, styrene/isoprene/styrene,styrene/ethylene-butylene/styrene or styrene/ethylene-propylene/styrene.

6. Graft copolymers of styrene or α-methylstyrene, for example styreneon polybutadiene, styrene on polybutadiene/styrene orpolybutadiene/acrylonitrile copolymers, styrene and acrylonitrile (ormethacrylonitrile) on polybutadiene; styrene, acrylonitrile and methylmethacrylate on polybutadiene; styrene and maleic anhydride onpolybutadiene; styrene, acrylonitrile and maleic anhydride or maleimideon polybutadiene, styrene and maleimide on polybutadiene, styrene andalkyl acrylates or alkyl methacrylates on polybutadiene, styrene andacrylonitrile on ethylene/propylene/diene terpolymers, styrene andacrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styreneand acrylonitrile on acrylate/butadiene copolymers and mixtures thereofwith the copolymers mentioned under 5), such as are known, for example,as so-called ABS, MBS, ASA or AES polymers.

7. Halogen-containing polymers, for example polychloroprene, chlorinatedrubber, chlorinated or chlorosulfonated polyethylene, copolymers ofethylene and chlorinated ethylene, epichlorohydrin homopolymers andcopolymers, in particular polymers formed from halogen-containing vinylcompounds, for example polyvinyl chloride, polyvinylidene chloride,polyvinyl fluoride or polyvinylidene fluoride; and copolymers thereof,such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl acetateor vinylidene chloride/vinyl acetate.

8. Polymers derived from α,β-unsaturated acids and derivatives thereof,such as polyacrylates and polymethacrylates, polyacrylamides andpolyacrylonitriles.

9. Copolymers of the monomers mentioned under 8) with one another orwith other unsaturated monomers, for example acrylonitrile/butadienecopolymers, acrylonitrile/alkyl acrylate copolymers,acrylonitrile/alkoxyalkyl acrylate copolymers, acrylonitrile/vinylhalide copolymers or acrylonitrile/alkyl methacrylate/butadieneterpolymers.

10. Polymers derived from unsaturated alcohols and amines or acylderivatives or acetals thereof, such as polyvinyl alcohol, polyvinylacetate, stearate, benzoate or maleate, polyvinylbutyral, polyallylphthalate or polyallylmelamine; and copolymers thereof with olefinsmentioned in item 1.

11. Homopolymers and copolymers of cyclic ethers, such as polyalkyleneglycols, polyethylene oxide, polypropylene oxide or copolymers thereofwith bisglycidyl ethers.

12. Polyacetals, such as polyoxymethylene, and also polyoxymethylenes ofthis type containing comonomers, for example ethylene oxide, andpolyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

13. Polyphenylene oxides and sulfides and mixtures thereof with styrenepolymers or polyamides.

14. Polyurethanes derived from polyethers, polyesters and polybutadieneshaving terminal hydroxyl groups on the one hand and from aliphatic oraromatic polyisocyanates on the other hand, and also precursors thereof.

15. Polyamides and copolyamides derived from diamines and dicarboxylicacids and/or from aminocarboxylic acids or the corresponding lactams,such as polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12 or 4/6,polyamide 11, polyamide 12 and aromatic polyamides formed from m-xylene,diamine and adipic acid; and polyamides prepared fromhexamethylenediamine and isophthalic and/or terephthalic acid and, ifappropriate, an elastomer as modifier, for examplepoly-2,4,4-trimethylhexamethyleneterephthalamide orpoly-m-phenyleneisophthalamide. Block copolymers of the polyamidesmentioned above with polyolefins, olefin copolymers, ionomers orchemically attached or grafted elastomers; or with polyethers, forexample polyethylene glycol, polypropylene glycol or polytetramethyleneglycol. Also polyamides or copolyamides modified with EPDM or ABS; andpolyamides which have been condensed during processing (“RIM polyamidesystems”).

16. Polyureas, polyimides, polyamide-imides and polybenzimidazoles.

17. Polyesters derived from dicarboxylic acids and dialcohols and/orfrom hydroxycarboxylic acids or the corresponding lactones, such aspolyethylene terephthalate, polybutylene terephthalate,poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoates andblock polyether esters derived from polyethers having hydroxyl endgroups; and also polyesters modified with polycarbonates or MBS.

18. Polycarbonates and polyester carbonates.

19. Polysulfones, polyether sulfones and polyether ketones.

20. Crosslinked polymers derived from aldehydes on the one hand andphenols, urea or melamine on the other hand, such asphenol/formaldehyde, urea/formaldehyde and melamine/formaldehyde resins.

21. Drying and non-drying alkyd resins.

22. Unsaturated polyester resins derived from copolyesters of saturatedand unsaturated dicarboxylic acids with polyhydric alcohols, and alsovinyl compounds as crosslinking agents, and also halogen-containingmodifications thereof of low flammability.

23. Crosslinkable acrylic resins derived from substituted acrylic acidesters, for example from epoxyacrylates, urethane acrylates or polyesteracrylates.

24. Alkyd resins, polyester resins and acrylate resins crosslinked withmelamine resins, urea resins, polyisocyanates or epoxy resins.

25. Crosslinked epoxy resins derived from polyepoxides, for example frombis-glycidyl ethers or cycloaliphatic diepoxides.

26. Natural polymers, such as cellulose, natural rubber, gelatine andthe polymer-homologously chemically modified derivatives thereof, suchas cellulose acetates, propionates and butyrates or the celluloseethers, such as methylcellulose; and also colophony resins andderivatives.

The use of the compounds according to the invention in coatings of alltypes is particularly preferred. These can be pigmented or unpigmentedcoatings or metal effect coatings. They can contain an organic solventor can be solvent-free or can be aqueous coatings.

The coatings can contain, as a binder, at least one of the polymerslisted above. The following are examples of coatings containing specialbinders:

1. Coatings based on cold-crosslinkable or hot-crosslinkable alkyd,acrylate, polyester, epoxy or melamine resins or mixtures of suchresins, if desired with an added acid curing catalyst;

2. Two-component polyurethane coatings based on acrylate, polyester orpolyether resins containing hydroxyl groups, and on aliphatic oraromatic polyisocyanates;

3. One-component polyurethane coatings based on masked polyisocyanateswhich are unmasked during baking;

4. Two-component coatings based on (poly)ketimines and aliphatic oraromatic polyisocyanates;

5. Two-component coatings based on (poly)ketimines and an unsaturatedacrylate resin or a polyacetoacetate resin or a methylmethacrylamidoglycolate;

6. Two-component coatings based on polyacrylates and polyepoxidescontaining carboxyl or amino groups;

7. Two-component coatings based on acrylate resins containing anhydridegroups, and on a polyhydroxyl or polyamino component;

8. Two-component coatings based on (poly)oxazolidines and acrylateresins containing anhydride groups, or unsaturated acrylate resins oraliphatic or aromatic polyisocyanates;

9. Two-component coatings based on unsaturated polyacrylates andpolymalonates;

10. Thermoplastic polyacrylate coatings based on thermoplastic acrylateresins or extraneously crosslinking acrylate resins in combination withetherified melamine resins;

11. Coating systems based on siloxane-modified or silane-modified orfluorine-modified acrylate resins.

The coatings can also be radiation-curable. In this case the binder iscomposed of monomeric or oligomeric compounds which contain ethylenicdouble bonds and are converted into a crosslinked, high-molecular formby irradiation with actinic light or with electron beams. In most casesthe binder is a mixture of such compounds. In radiation-curable coatingsthe compounds of formula I can be used also in absence of a stericallyhindered amine.

The coatings can be applied as one-coat or two-coat systems, it beingpreferable to add the stabilizers according to the invention to theunpigmented top coat.

The coatings can be applied to the substrates (metal, plastic, wood,etc.) by the customary processes, for example by brushing, spraying,curtain-coating, dipping or electrophoresis.

The amount of (a) and (b) added depends on the substrate and therequirements for its stability. In general, 0.01 to 5% by weight, inparticular 0.02 to 2% by weight, of the component (a) and 0.02 to 5% byweight, in particular 0.05 to 3% by weight, of the component (b) areadded, relative to the polymer.

The two components can be added on their own or as a mixture. Additionis preferably carried out before or during the shaping of the polymer.It can also be carried out as early as the preparation of the polymer,for example before or during polymerization.

The compounds of the formula Ia can also be used on their own, ie.without a sterically hindered amine, for stabilizing organic polymers.In this case 0.01 to 10% by weight, for example, preferably 0.05 to 5%by weight, of a compound of the formula Ia is added to the polymer. Theuse of compounds of the formula Ia as a stabilizer for polycarbonates isof particular interest.

In addition to the stabilizers, according to the invention, of theformula Ia or the stabilizer combination (a)+(b), it is also possible toadd other stabilizers to the polymer. The following are examples ofthese:

1. Antioxidants

1.1. Alkylated monophenols, for example2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol,2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,2,6-di-tert-butyl4-isobutylphenol, 2,6-di-cyclopentyl-4-methylphenol,2-(α-methylcyclohexyl)-4,6-dimethylphenol,2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,2,6-di-tert-butyl-4-methoxymethylphenol and 2,6-di-nonyl-4-methylphenol.

1.2. Alkylated hydroquinones, for example2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,2,5-di-tert-amylhydroquinone and 2,6-diphenyl-4-octadecyloxyphenol.

1.3. Hydroxylated thiodiphenyl ethers, for example2,2′-thiobis-(6-tert-butyl-4-methylphenol),2,2′-thiobis-(4-octylphenol),4,4′-thiobis-(6-tert-butyl-3-methylphenol),4,4′-thiobis-(6-tert-butyl-2-methylphenol).

1.4. Alkylidene bislphenols, for example2,2′-methylenebis-(6-tert-butyl-4-methylphenol),2,2′-methylenebis-(6-tert-butyl-4-ethylphenol),2,2′-methylenebis-[4-methyl-6-(α-methylcyclohexyl)-phenol],2,2′-methylenebis-(4-methyl-6-cyclohexylphenol),2,2′-methylenebis-(6-nonyl-4-methylphenol),2,2′-methylenebis-(4,6-di-tert-butylphenol),2,2′-ethylidenebis-(4,6-di-tert-butylphenol),2,2′-ethylidenebis-(6-tert-butyl-4-isobutylphenol),2,2′-methylenebis-[6-(α-methylbenzyl)-4-nonylphenol],2,2′-methylenebis-[6-(α,α-dimethylbenzyl)-4-nonylphenol],4,4′-methylenebis-(2,6-di-tert-butylphenol),4,4′-methylenebis-(6-tert-butyl-2-methylphenol),1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane,2,6-bis-(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,1,1,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane,1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane,ethylene glycol bis-[3,3-bis-(3′-tert-butyl-4′-hydroxyphenyl)-butyrate],bis-(3-tert-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene andbis-[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate.

1.5. Benzyl compounds, for example1,3,5-tris-(3,5di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,bis-(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate,bis(4-tert-butyl-3-hydroxy-2,6-methylbenzyl)-dithiol terephthalate,1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,1,3,5-tris-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate,dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, the Ca salt ofmonoethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate and1,3,5-tris-(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.

1.6. Acylaminophenols, for example 4-hydroxylauranilide,4-hydroxystearanilide,2,4-bis-(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyaniline-s-triazineand octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamate.

1.7. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid,with monohydric or polyhydric alcohols, for example methanol,octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol,diethylene glycol, triethylene glycol, pentacrythritol,tris-(hydroxyethyl)isocyanurate and N,N′-bis-(hydroxyethyl)oxamide.

1.8. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acidwith monohydric or polyhydric alcohols, for example methanol,octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol,diethylene glycol, triethylene glycol, pentaerythritol,tris-(hydroxyethyl) isocyanurate and N,N′-bis-(hydroxyethyl)oxamide.

1.9. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)-propionic acid withmonohydric or polyhydric alcohols, for example methanol, octadecanol,1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethyleneglycol, triethylene glycol, pentaerythritol, tris-(hydroxyethyl)isocyanurate and N,N′-bis-(hydroxyethyl)oxamide.

1.10. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid,for exampleN,N′-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylenediamine,N,N′-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-trimethylenediamineand N,N′-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazine.

2. UV absorbers and light stabilizers

2.1. 2-(2′-hydroxyphenyl)-benzotriazoles, for example the 5′-methyl-,3′,5′-di-tert-butyl-, 5′-tert-butyl-, 5′-(1,1,3,3-tetramethylbutyl)-,5-chloro-3′,5′-di-tert-butyl-, 5-chloro-3′-tert-butyl-5′-methyl-,3′-sec-butyl-5′-tert-butyl-, 4′-octoxy-, 3′,5′-di-tert-amyl-,3′,5′-bis-(α,α-dimethylbenzyl)- derivative.

2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy-, 4-methoxy-,4-octoxy-, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy-, 4,2′,4′-trihydroxy-or 2′-hydroxy-4,4′-dimethoxy- derivative.

2.3. Esters of unsubstituted or substituted benzoic acids, for example4-tert-butylphenyl salicylate, phenyl salicylate, octylphenylsalicylate, dibenzoylresorcinol, bis-(4-tert-butylbenzoyl)-resorcinol,benzoylresorcinol, 2,4-di-tert-butylphenyl3,5-di-tert-butyl-4-hydroxybenzoate and hexadecyl3,5-di-tert-butyl-4-hydroxybenzoate.

2.4. Acrylates, for example ethyl or isooctylα-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl orbutyl α-cyano-β-methyl-p-methoxycinnamate, methylα-carbomethoxy-p-methoxycinnamate orN-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

2.5. Nickel compounds, for example nickel complexes of2,2′-thiobis-[4-(1,1,3,3-tetramethylbutyl)-phenol], such as the 1:1complex or the 1:2 complex, if appropriate with additional ligands, suchas n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickeldibutyldithiocarbamate, nickel salts of monoalkyl4-hydroxy-3,5-di-tert-butylbenzylphosphonates, such as the methyl orethyl ester, nickel complexes of ketoximes, such as2-hydroxy-4-methylphenyl undecyl ketoxime, or nickel complexes of1-phenyl-4-lauroyl-5-hydroxypyrazole, if appropriate with additionalligands.

2.6. Oxamides, for example 4,4′-di-octyloxyoxanilide,2,2′-di-octyloxy-5,5′-di-tert-butyloxanilide,2,2′-di-dodecyloxy-5,5′-di-tert-butyloxanilide,2-ethoxy-2′-ethyloxanilide, N,N′-bis-(3-dimethylaminopropyl)-oxalamide,2-ethoxy-5-tert-butyl-2′-ethyloxanilide and a mixture thereof with2-ethoxy-2′-ethyl-5,4′-di-tert-butyloxanilide or mixtures of o-methoxy-and p-methoxy-disubstituted oxanilides and of o-ethoxy- andp-ethoxy-disubstituted oxanilides.

3. Metal deactivators, for example N,N′-diphenyloxamide,N-salicylal-N′-salicyloylhydrazine, N,N′-bis-(salicyloyl)-hydrazine,N,N′-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazine,3-salicyloylamino-1,2,4-triazole and bis-(benzylidene)-oxalic aciddihydrazide.

4. Phosphites and phosphonites, for example triphenyl phosphite,diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris-(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris-(2,4-di-tert-butylphenyl) phosphite,diisodecyl pentaerythritol diphosphite, bis-(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite,tetrakis-(2,4-di-tert-butylphenyl) 4,4′-biphenylene diphosphonite and3,9-bis-(2,4-di-tert-butylphenoxy)-2,4,8,1-tetraoxa-3,9-diphosphaspiro[5.5]undecane.

5. Compounds which destroy peroxides, for example esters ofβ-thiodipropionic acid, for example the lauryl, stearyl, myristyl ortridecyl esters, mercaptobenzimidazole, the zinc salt of2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyldisulfide and pentaerythritol tetrakis-(β-dodecylmercapto)propionate.

6. Polyamide stabilizers, for example copper salts in combination withiodides and/or phosphorus compounds and salts of divalent manganese.

7. Basic co-stabilizers, for example melamine, polyvinylpyrrolidone,dicyandiamide, triallyl cyanurate, urea derivatives, hydrazinederivatives, amines, polyamides, polyurethanes, alkali and alkalineearth salts of higher fatty acids, for example Ca stearate, Zn stearate,Mg stearate, Na ricinoleate and K palmitate, antimony pyrocatecholate ortin pyrocatecholate.

8. PVC stabilizers, for example organotin compounds or salts of barium,cadmium, zinc and led.

Other materials such as are customary in the technology of plastics andpaints can also be added. Examples of these are fillers and reinforcingagents, pigments, dyes, plasticizers, solvents, lubricants, flow-controlagents, fluorescent brighteners, nucleating agents, antistatic agents orfire-retarding agents.

The invention also relates, therefore, to organic polymers containing,as stabilizers, a sterically hindered amine of the polyalkylpiperidinetype and a hydroxyphenyltriazine of the formula I, and also to organicpolymers containing a compound of the formula Ia as the stabilizer.

The polymers stabilized in this manner can be used in various shapes,for example as films, fibres, tapes, mouldings, profiles, latex,dispersions, paints or cements.

The following examples illustrate the invention in greater detailwithout intending to limit it to the examples. Parts and percentages areparts by weight and percentages by weight.

PREPARATION EXAMPLES Example 1

23.8 g (0.06 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazine(prepared as described in U.S. Pat. No. 3,244,708 Example 16) aresuspended in 300 ml of xylene. 12.1 g (0.09 mol) of 97% butyl glycidylether and 0.75 g (0.006 mol) of dimethylbenzylamine are added to thissuspension, and the mixture is heated to reflux temperature. After areaction time of 5 hours the clear, brownish solution is cooled andclarified by filtration through 100 g of silica gel. The yellow solutionis evaporated and the residue is recrystallized from hexane/toluene.This gives 27.3 g of pale yellow crystals of2-[2-hydroxy-4(3-butoxy-2-hydroxypropyloxy)-phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin(=86% yield). Melting point: 80-83° C. (Compound 1).

In analogous manner the compounds 2 to 28, listed in Table 1, areobtained from2-(2,4-dihydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine andan epoxy compound.

TABLE 1

Compound n R₇ Physical data  1 1 —CH₂CH(OH)CH₂OC₄H₉ m.p. 80-83° C.  2 1—CH₂CH(OH)CH₂OCOC(CH₃)═CH₂ m.p. 100-103° C.  3 2—CH₂CH(OH)CH₂O—(CH₂)₄—OCH₂CH(OH)CH₂— m.p. 150-152° C.  4 1

m.p. 115-117° C.  5 1 —CH₂CH(OH)CH₂—OH m.p. 165-167° C.  6 1

m.p. 101-104° C.  7 1

m.p. 75-77° C.  8 1

Oil found: C: 75.6% H:  9.2%   calc: C: 75.9% H:  9.1%  9 2

m.p. 100-103° C. 10 1 —CH₂CH(OH)(CH₂)₁₁CH₃ m.p. 102-104° C. 11 1—CH₂CH(OH)(CH₂)₇CH₃ m.p. 97-99° C. 12 1

Oil found: C: 64.9% H:  7.6% N:  4.4%   calc.: C: 66.7% H:  7.16% N: 5.4% 13 1

Oil found: calc.:   N: 3.75% N: 3.43% 14 2

Oil found: calc.:   N: 5.17% N: 5.18% 15 1 —CH₂CH(OH)CH₂OCOC₉H₁₉ Oilfound: N: 6.3% calc.: N: 6.7% 16 1

m.p. 152-155° C. 17 1 —CH₂CH(OH)CH₂O(C₁₃H₂₇ to C₁₅H₃₁) Oil MS, NMR 18 1—CH₂CH(OH)CH₂O(C₁₂H₂₅ to C₁₄H₂₉) Oil MS, NMR 19 2

Resin found: calc.   C = 71.3%, H = 6.6% C = 71.4%, H = 6.6% 20 1—CH₂CH(OH)CH₂OCOC₁₀H₂₁-tert. Resin MS, NMR 21 1 —CH₂CH(OH)CH₂OCH₂CH═CH₂m.p. 94-95° C. 22 1 —CH₂CH(OH)CH₃ m.p. 151-153° C. 23 1

m.p. 99-101° C. 24 2

Resin found: calc.:   N = 8.2% N = 8.3%

Example 2

22.1 g (0.05 mol) of2-(2-hydroxy-4-hydroxyethoxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine(prepared as described in U.S. Pat. No. 3,244,708, Example 18), aredissolved in 300 ml of tetrahydrofurane at 40° C. and 21 ml (0.15 mol)of triethylamnine are added. A solution of 5.05 ml (0.053 mol) ofacrylic acid chloride in 20 ml THF is added dropwise with stirring andwith cooling the reaction mixture to 25-30° C. After further stirring oftwo hours the precipitated ammonium salt is filtered off, the filtrateis evaporated and the residue recrystallized from toluene-hexane mixtureto obtain 22 g (88.7% yield) of2-(2-hydroxy-4-acryloyloxyethoxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazineas slightly yellow crystals (compound No. 25), m.p. 128-129° C.

In analogous manner the compounds No. 26 and 27 were prepared.

Compound n R₇ Phys. data 25 1 —CH₂CH₂OCOCH═CH₂ m.p. 128-129° C. 26 1—CH₂CH(CH₃)OCOCH═CH₂ m.p. 128-129° C. 27 1 —CH₂CH₂OCOCH(CH₃)═CH₂ m.p.128-129° C.

Example 3

20 g (0.04 mol) of2-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-4,6-bis-(2,4)-dimethylphenyl)-1,3,5-triazine(prepared as described in U.S. Pat. No. 3,244,708, Example 19), aredissolved in 100 ml of toluene, and 5 g (0.048 mol) of 2-methylpentanoland 0.5 g of dibutyltin oxide as catalyst are added, and the mixture isheated to reflux temperature. In the course of this a toluenelethanolmixture is distilled off. The toluene is replenished dropwise from adropping funnel. The transesterification reaction is complete after 2hours. The solution is cooled and filtered through 80 g of silica geland is then evaporated. The residue is recrystallized from ethanol. Thisgives 14 g of the compound 28 (see Table 2). Melting point: 87-89° C.

Compounds 29 to 37 are obtained analogously by transesterification withthe corresponding alcohols.

TABLE 2

Compound R₈ Physical data 28

m.p. 87-89° C. 29 —CH₂CH₂CH₂CH₃ m.p. 136-138° C. 30 —C₈H₁₇ (isomermixture) Waxlike calcd. C 74.05% H 7.28% N 7.4% found C 73.98% H 7.36% N7.3% 31

Oil calcd. found   C 64.47% C 64.75%   H 6.99% H 7.00%   N 5.50% N 5.72%32 —C₁₀H₂₁ (isomer mixture) Waxlike calcd. C 74.59% H 7.61% N 7.05%found C 74.76% H 7.73% N 6.89% 33

Resin calcd. found   C 70.45% C 70.12%   H 7.06% H 7.02%   N 6.85% N6.84% 34

m.p. 75-78° C. 35 —(CH₂)₈CH═CH—(CH₂)₇—CH₃ Waxlike calcd. C 76.96% H8.42% N 5.95% found C 77.02% H 8.47% N 5.74% 36 —(CH₂)₂O(CH₂)₂OC₆H₁₃Resin calcd. C 70.68% H 7.37% N 6.68% found C 70.53% H 7.49% N 6.39% 37

Resin calcd. found   C 63.44% C 63.54%   H 7.22% H 7.20%   N 4.93% N5.01%

Example 4

9.1 g (0.02 mol) of2-(2-hydroxy-4-carboxymethoxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine(prepared as described in U.S. Pat. No. 3,244,708, Example 16) aresuspended in 40 ml of thionyl chloride, and 1 ml of DMF is added. Themixture is heated at reflux temperature for 2 hours. A clear yellowsolution is formed with moderate evolution of gas. This solution isevaporated to give 9.5 g of[4-(4,6-di-2′,4′-xylyl-s-triazin-2-yl)-3-hydroxyphenoxy]-acetyl chloride(Compound 38). This acid chloride is dissolved in 100 ml of toluene.19.3 g (0.08 mol) of bis-(2-ethylhexyl)-amine are added dropwise at roomtemperature. The reaction proceeds exothermically from 22° C. to 40° C.The mixture is left for 1 hour at room temperature to complete thereaction. The product is then purified by column chromatography oversilica gel. This gives approx. 5 g of a pale yellow, highly viscous oil,[4-(4,6-di-2′,4′-xylyl-s-triazin-2-yl)-3-hydroxyphenoxy]-acetic acidbis-(2-ethylhexyl)-amide (Compound 39).

Calcd. C, 76.07%, H, 8.61%, N, 8.25%. Found. C, 75.91%, H, 8.46%, N,8.16%.

Example 5

39.7 g (0.1 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine aredissolved in 250 ml of DMF. 20.7 g of potassium carbonate are added tothis brownish solution. An orange suspension is formed. 17 g (0.052 mol)of 1,12-di-bromododecane are added and the mixture is heated at 100° C.The reaction is complete after 2 hours. The cooled reaction solution isthen poured into 1.51 of water, and the precipitate is filtered off andwashed with 2-3 times 100-200 ml of H₂O. The crystals are thenrecrystallized from xylene. Melting point: 158-163° C. (Compound 40).

Compounds 41 and 42 are obtained analogously, using 1,6-dibromohexane,1,4-dichloro-2-butene and p-xylylenedibromid.

TABLE 3

Compound R₇ Physical data 40 —(CH₂)₁₂— m.p. 158-163° C. 41 —(CH₂)₆— m.p.203-205° C. 42 —CH₂—CH═CH—CH₂— m.p. 230-235° C. 43

m.p. 252-254° C.

Example 6

20 g (0.05 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine aresuspended in 100 ml of toluene, and 100 ml of 1N NaOH and 1 g oftetrabutylammonium bromide are added. The mixture is heated for 10minutes at 80° C. and then cooled, to give a yellow paste. 12.3 ml (0.15mol) of epibromohydrin are added to this paste and the mixture is againheated for 6 hours at 50° C. When the reaction is complete, methylenechloride is added to the organic phase, which is separated off from theaqueous phase and filtered through Hyflo. It is then evaporated and thecrystalline residue is recrystallized from toluene. This gives 14 g ofpale yellow crystals,2-(2-hydroxy-4-glycidyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine(Compound 44), melting point 152-155° C.

Example 7

9.07 g (0.02 mol) of Compound 44 and 7.95 g (0.02 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine aresuspended in 150 ml of xylene. 0.2 g of dimethylaminopyridine are addedand the mixture is heated at reflux temperature. The reaction iscomplete after 4 hours. The mixture is diluted with 200 ml of tolueneand cooled. In the course of this the product is precipitated. It isfiltered off and purified further by recrystallization from toluenetogether with a little Fuller's earth. This gives 9.1 g of pale beigecrystals,1,3-bis-{4-[4,6-di-(2,4-dimethylphenyl)-s-triazine-2-yl]-3-hydroxy-phenoxy}-2-hydroxypropane(Compound 45), melting point: 222-224° C.

Example 8

18.5 g (0.05 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine (Helv.Chim. Acta 55, 1566 (1972)) and 3.9 g (0.05 mol) of potassium methoxideare suspended in 200 ml of anhydrous n-butanol, and 7.4 g (0.06 mol) ofbutyl chloroacetate are added dropwise between 50° C. and 100° C. After17 hours under reflux the solvent is evaporated and the crude product iswashed with water, dried and recrystallized from petroleum ether(boiling point 110° C.-140° C.) (Compound No. 46). Melting point:142-146° C.

Calcd. C, 72.03; H, 6.04; N, 8.69%. Found C, 71.88; H, 6.01; N, 8.81%.

Example 9

A) 55.4 g (0.15 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine aredissolved in refluxing 2-butanone (1 l) in the presence of 27.6 g (0.2mol) of K₂CO₃. A catalytic amount (0.2 g) of KI is added, and 36.8 g(0.3 mol) of ethyl chloroacetate are added dropwise over 1 h 30. Afterrefluxing for 25 h, the reaction mixture is cooled in ice, theprecipitate is filtered off, washed with water to neutrality and thenwith methanol. Drying in the oven yields the analytically pure2-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine(54 g, m.p. 166-167° C.) (Compound No. 47).

B) 11.4 g (0.025 mol) of compound 47 and 3.9 g (0.03 mol) of octanol(isomeric mixture) are refluxed in 120 ml xylene for 22 h in thepresence of 0.62 g (2.5 mmol) of dibutyltinoxide. During the reaction axylene/ethanol mixture is distilled off, the xylene being replenisheddropwise from a dropping funnel. The reaction mixture is cooled to 40°C., filtered through a pad of Prolith and evaporated. Drying at 100°C./0.01 mmHg affords the transesterification product as a viscous yellowoil (12.5 g) that solidifies to a wax (Compound No. 48).

Calcd. C=73.44%, H=6.91%, N=7.79%. Found C=72.95%, H=6.70%, N=7.48%.

Compounds No. 49 to 52 (Table 4) are obtained analogously bytransesterification with the corresponding alcohols.

TABLE 4

Compound n R₇ Physical data 49 1 —CH₂CH₂OCH₃ m.p. 150-153° C. 50 2—CH₂CH₂OCH₂CH₂OC₂H₅ m.p. 118-121° C. 51 2 —(CH₂)₆— m.p. 235-238° C. 52 4

m.p. 219-231° C.

Example 10

40.6 g (0.11 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine aredissolved in refluxing 2-butanone (500 ml) in the presence of 20.7 g(0.15 mol) of K₂CO₃. 18.1 g (0.055 mol) of 1,12-dibromodecane dissolvedin 100 ml of 2-butane are added dropwise over 3 h and the mixture isrefluxed for 35 h. In the course of this precipitation of the finalproduct occurs. The reaction mixture is cooled in ice, the precipitateis filtered off, washed with water to neutrality and then with methanol.Drying in the oven affords 46.2 g of the analytically pure compound No.53 (Table 5). Off-white solid. m.p. 219-220° C.

Analogous treatment with 1,6-dibromohexane or epibromohydrin givescompounds No. 54 and 55 (Table 5).

TABLE 5

Compound n R₇ Physical data 53 2 —(CH₂)₁₂— m.p. 219-220° C. 54 2—(CH₂)₆— m.p. 247-249° C. 55 1

m.p. 205-208° C. 56 1

m.p. 166-167° C. 57 1

m.p. 123-125° C. 58 1

Yellow oil calc. C 66.02% H  6.89% N  5.63%   found 64.52%  6.98%  5.23%59 1

m.p. 183-185° C. 60 1

m.p. 135-138° C. 61 2 —OC—(CH₂)₈—CO— m.p. 220-228° C.

Example 11

A mixture of 14.8 g (0.04 mol) of2-(2,4-dihydroxyphenyl)-4,6bis-(4-methylphenyl)-1,3,5-triazine, 10.4 g(0.08 mol) of butylglycidylether and 2.1 g (6.5 mmol) oftetratbutylammoniumbromide is refluxed in 150 ml of 2-butanone during 85h. The reaction mixture is cooled in ice, the precipitate is filteredoff, washed with water and methanol, and dried in the oven. This yields17.5 g of a pale yellow solid, m.p. 166-167° C. (Compound No. 56, Table4).

Analogous treatment with the corresponding glycidyl ethers or estersyields the compounds 57 to 60 (Table 4).

Example 12

A solution of 3.6 g (0.015 mol) of sebacyl chloride in 10 ml toluene isadded dropwise at 10° C. to a solution of2-(2,4-dihydroxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine and 3.3 g(0.033 mol) of triethylamine in 100 ml toluene and 50 ml of DMF. After50 h at room temperature, the reaction mixture is diluted with water,filtered, the precipitate is washed with water, methanol and chloroform,and dried in the oven. 8.7 g of the diester 61 (Table 4) are obtained asa pale beige solid, m.p. 220-228° C.

Example 13

When 20.5 g (0.06 mol) of2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine are treated with22.8 g (0.12 mol) of 2-ethylhexyl glycidyl ether analogously to example11, 23.3 g of the pale yellow compound No.62 (m.p. 116 to 118° C.) areobtained.

Example 14

7.9 g (0.02 mol) of2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 5.7g (0.02 mol) of a technical mixture of dodecyl, tridecyl and tetradecylglycidyl ethers (Araldite® DY 025) and 0.15 g of ethyltriphenylphosphonium iodide in 50 ml of mesitylene are heated at160-165° C. for 10 hours, with stirring. The reaction solution is washedwith water, dried over MgSO₄ and filtered. The filtrate is stirred for 2hours with 2 g of Filtrol 4, filtered and evaporated in vacuo. Theresidue is freed from residual mesitylene at 120° C. and 0.01 mmHg. Thisleaves 12.1 g of an oil (Compound No. 63).

C₄₁H₅₅N₃O₄ Calcd. C 75.30 H 8.48 N 6.43% Found. C 75.0 H 8.1 N 6.8%

APPLICATION EXAMPLES Example 15 Stabilization of a 2-Coat MetallicCoating

A clear lacquer is prepared by mixing the following components:

59.2 Parts of a commercial acrylic resin (Uracron ® XB 2263, DMS ResinsBV, NL) which is a 50% solution in xylene, 11.6 parts of a 90% melamineresin (Cymel ® 327, Amer. Cyanamid Corp.) 19.4 parts of xylene 5.5 partsof butylgylcol acetate 9.3 parts of butanol 1.0 parts of a levelingagent (Baysilon ® A, Bayer AG) which is a 1% solution in xylene 100parts lacquer containing 40% solids.

Samples of this laquer are mixed with 0.5% (related to the solids) ofdi(1,2,2,6,6-pentamethylpiperidin-4-yl)sebacate (=HA-1) and 1,5%(related to the solids) of a triazine stabilizer listed in table 6.

The clear lacquer is diluted to a sprayable state with a mixture of13:6:1 xylene/butanol/butyl glycol acetate and is sprayed onto apreviously prepared aluminum sheet (coil-coated and primed with asilver-metallic paint based on polyester/celluloseacetobutyrate/melamine resin), and the sheet is baked for 30 minutes at130° C. This results in a dry film thickness of 40-50 μm of clearlacquer. A clear lacquer containing no light stabilizer is used as acomparison.

The samples are exposed in a UVCON, Type UVB-313, weathering equipmentwith a cycle of 8 hrs of dry UV irradiation at 70° C. and 4 hrs ofcondensation at 50° C. The 20°-gloss of the samples is measured incertain intervals of weathering time using the method of DIN 67530. Theresults are given in Table 6.

TABLE 6 20°-Gloss after exposure of Piperidin Triazine Stabilizer hrsStabilizer (Compound No.) 0 1600 3200 4800 6400 — — 86 31 — — — 0.5%HA-1 1.5% 1 86 79 74 77 61 0.5% HA-1 1.5% 30 86 74 68 66 57 0.5% HA-11.5% 32 82 69 72 68 59 0.5% HA-1 1.5% 33 85 79 74 72 64

Example 16

The preparation of the samples and their testing is the same as inExample 15. As comparison C-1 and C-2, two triazine derivatives knownfrom U.S. Pat. No. 4,619,956, are used as triazine stabilizers.

C-1=2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-diphenyl-1,3,5-triazine

C-2=2-(2-hydroxy-4-octadecyloxyphenyl)-4,6-diphenyl-1,3,5-triazine

The results are shown in Table 7.

TABLE 7 20°-Gloss after exposure of Piperidin hrs Stabilizer TriazineStabilizer 0 1600 3200 4000 — — 84 19 — — 0.5% HA-1 1.5% Compound 34 8480 78 59 0.5% HA-1 1.5% Compound 35 85 81 80 75 0.5% HA-1 1.5% Compound36 85 80 78 76 0.5% HA-1 1.5% Compound 37 85 80 79 77 0.5% HA-1 1.5%Compound 39 85 81 72 74 0.5% HA-1 1.5% C-1 85 54 35 37 0.5% HA-1 1.5%C-2 79 38 34 37

Example 17

A similar clear lacquer is prepared from

54.5 parts of Uracron ® XB 2263 16.3 parts of Cymel ® 327 19.4 parts ofxylene 5.5 parts of butylgylcol acetate 3.3 parts of butanol 1 part ofBaysilon ® A 100 parts lacquer containing 41.5% solids.

Samples of this laquer are mixed with 0.5% (related to the solids) ofHA-1 and 1.5% (related to the solids) of a triazine stabilizer listed inTable 8. The lacquer is diluted to a sprayable state by diluting with a13:6:1 mixture of xylene/butanol/butylglycol acetate and is sprayed ontoan aluminium sheet which is coil coated and primed with a metallic bluecommercial paint (Glasomax®, Glasurit GmbH, Münster). After baking for30 minutes at 130° C. the clear lacquer layer has a thickness of 40-45μm.

The samples are weathered in a UVCON, Type UVB 313, as described inExample 15 and the 20°-gloss of the weathered samples is measuredaccording to method DIN 67530. The results are shown in Table 8.

TABLE 8 20°-Gloss after exposure of Piperidin Triazine Stabilizer hrsStabilizer (Compound No.) 0 800 1600 2000 — — 85 75 42 20 0.5% HA-1 1.5%4 86 80 78 78 0.5% HA-1 1.5% 6 87 81 81 81 0.5% HA-1 1.5% 7 85 81 81 790.5% HA-1 1.5% 10 86 82 80 80 0.5% HA-1 1.5% 11 86 81 81 78 0.5% HA-11.5% 17 86 81 8I 81 0.5% HA-1 1.5% 18 87 81 80 80 0.5% HA-1 1.5% 62 8480 78 81

Example 18

Two-coat samples are prepared as described in Example 15, however, nopiperidin stabilizer is added. The samples are weathered in aWeatherometer with cycle CAM 159 and with using an edge filter of typeA. Measured is the 20°-gloss before and after exposure, the results areshown in Table 9.

TABLE 9 20°-Gloss after exposure of Triazine Stabilizer hrs (CompoundNo.) 0 2000 3600 none 85 47 25 34 86 71 64 35 86 72 61 36 86 73 60

Example 19

Two-coat samples are prepared as described in Example 17, however, nopiperidin stabilizer is added. The samples are weathered in a UVCON,type UVB-313 with cycle of 8 hrs of UV irradiation at 70° C. and 4 hrsof condensation at 50° C. The 20°-gloss of the sample is measuredaccording to method DIN 67530 before and after exposure. Further thechange of colour shade ΔE after exposure is measured according to methodDIN 6174. The results are shown in Table 10.

TABLE 10 20°-Gloss after exposure of Triazine Stabilizer hrs ΔE(Compound No.) 0 800 1600 after 1600 h none 85 75 42 6.6 6 84 80 80 1.37 84 81 80 1.3 17 86 81 80 1.6 18 86 81 80 1.4 62 86 82 81 1.0

Example 20 Stabilization of a Radiation-curable System

A clear laquer is prepared by mixing 14 parts oftris(2-acryloyloxyethyl)isocyanurate with 6 parts of 1,6-hexanedioldiacrylate and 0.4 parts of 1-benzoylcyclohexanol (as photoinitiator). Atriazine stabilizer is added in an amount of 1.5%. The lacquer is coatedto a white coil-coated aluminium sheet in a dry-thickness of about 40μm.

The samples are hardened by UV irradiation in a PPG processor (2×80W/cm, 2×10 m (min) and weathered in a UVCON, type UVB-313 with a cycleof 4 hours of UV irradiation at 60° C. and 4 hrs of condensation at 50°C.

The yellowness index (method ASTM D 1925-70) of the samples is measuredbefore and after the exposure. The results are shown in Table 11.

TABLE 11 Yellowness Index after exposure of Triazine Stabilizer hrs(Compound No.) 0 200 400 600 none −1.0 19.6 28.0 35.3 1.5% 17 −0.6 1.81.8 2.1

What is claimed is:
 1. An organic material which has been stabilizedagainst damage caused by light, heat and oxygen and which contains (a)at least one sterically hindered amine of the polyalkylpiperidine typeand (b) at least one o-hydroxyphenyl-s-triazine, wherein the triazinecompound (b) is a compound of the formula I

 in which n is 1 to 4, R₁ and R₂ independently of one another are H, OH,C₁-C₁₂alkyl, cyclohexyl or trifluoromethyl, R₃ and R₄ independently ofone another are H, OH, C₁-C₁₂alkyl, cyclohexyl, C₁-C₁₈alkoxy or halogenand, in the event that n=1, can also be a radical —OR₇, R₅ and R₆independently of one another are H, C₁-C₁₂alkyl or halogen, R₇, if n is1, is a) C₁-C₁₈alkyl which is substituted by one or more of the groupsOH, C₁-C₁₈alkoxy, C₃-C₁₈alkenoxy, halogen, phenoxy (which isunsubstituted or substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen),furyloxy,

 —COOH, —COOR₈, —CONH₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, —N, —N(R₉)(R₁₀),—NHCOR₁₁, —CN and/or by —O—CO—R₁₁, b) C₄-C₅₀alkyl which is interruptedby one or more O and can be substituted by OH or/and glycidyloxy, c)C₃-C₆alkenyl, d) glycidyl or a group

e) cyclohexyl which is unsubstituted or substituted by OH or —OCOR₁₁, f)C₇-C₁₁phenylalkyl which is unsubstituted or substituted by OH, Cl orCH₃, g) —CO—R₁₂ or h) —SO₂—R₁₃,  and if n is 2, R₇ is a) C₂-C₁₆alkylene,b) C₄-C₁₂alkenylene, c) xylylene, d) C₃-C₂₀alkylene which is interruptedby one or more O and/or substituted by OH, e) a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—, —CO—NH—R₁₇—NH—CO— or—(CH₂)_(m)—COO—R₁₈—OOC—(CH₂)_(m)— (in which m is 1 to 3) or

 and if n is 3, R₇ is a group

 and if n is 4, R₇ is a group

R₈ is C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₃-C₂₀alkyl which is interrupted byone or more O, N or S and/or substituted by OH, C₁-C₄alkyl which issubstituted by —P(O)(OR₁₄)₂, —N(R₉)(R₁₀) or —OCOR₁₁ and/or OH,C₃-C₁₈alkenyl, glycidyl or C₇-C₁₁phenylalkyl, R₉ and R₁₀ independentlyof one another are C₁-C₁₂alkyl, C₃-C₁₂alkoxyalkyl,C₄-C₁₆dialkylaminoalkyl or C₅-C₁₂cycloalkyl, or R₉ and R₁₀ together areC₃-C₉alkylene or C₃-C₉oxaalkylene or C₃-C₉azaalkylene, R₁₁ isC₁-C₁₈alkyl, C₂-C₁₈alkenyl or phenyl, R₁₂ is C₁-C₁₈alkyl, C₂-C₁₈alkenyl,phenyl, C₁-C₁₂alkoxy, phenoxy, C₁-C₁₂alkylamino or C₆-C₁₂arylamino or agroup —R₂₄—COOH or —NH—R₁₇—NCO, R₁₃ is C₁-C₁₂alkyl, C₆-C₁₂aryl orC₇-C₁₄alkaryl, R₁₄ is C₁-C₁₂alkyl or phenyl, R₁₅ is C₂-C₁₀alkylene,C₄-C₅₀alkylene which is interrupted by one or more O, phenylene or agroup -phenylene-X-phenylene- in which X is —O—, —S—, —SO₂—, —CH₂— or—C(CH₃)₂—, R₁₆ is C₂-C₁₀alkylene, C₂-C₁₀oxaalkylene orC₂-C₁₀thiaalkylene, C₆-C₁₂arylene or C₂-C₆alkenylene, R₁₇ isC₂-C₁₀alkylene, phenylene, tolylene, diphenylenemethane or a group

R₁₈ is C₂-C₁₀alkylene or C₄-C₂₀alkylene which is interrupted by one ormore O, R₁₉ is C₃-C₁₂alkanetriyl, R₂₀ is C₄-C₁₂alkanetetryl, R₂₃ isC₂-C₁₀alkylene, phenylene or a group

 wherein X is O, S, SO₂, CH₂ or C(CH₃)₂, and R₂₄ is C₂-C₁₄alkylene,vinylene or o-phenylene.
 2. An organic material according to claim 1,wherein the triazine compound (b) is a compound of the formula I inwhich n is 1 to 4, R₁ and R₂ independently of one another are H, OH orC₁-C₄alkyl, R₃ and R₄ independently of one another are H, OH,C₁-C₄alkyl, C₁-C₄alkoxy, halogen or a radical —OR₇, R₅ and R₆independently of one another are H or C₁-C₄alkyl, R₇, if n is 1, is a)C₁-C₁₈alkyl which is substituted by one or more of the groups OH,C₁-C₁₈alkoxy, allyloxy, phenoxy, furyloxy,

—COOR₈, —CON(R₉)(R₁₀) and/or by —OCOR₁₁, b) C₄-C₅₀alkyl which isinterrupted by one or more O and can be substituted by OH or/andglycidyloxy, c) allyl, glycidyl or benzyl, d) cyclohexyl orhydroxycyclohexyl,  and if n is 2, R₇ is C₄-C₁₂alkenylene,C₄-C₆alkenylene, xylylene, C₃-C₂₀alkylene which is interrupted by one ormore O and/or substituted by OH, or R₇ is a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—, —CH₂—COO—R₁₈—OOC—CH₂— or

 and if n is 3, R₇ is a group

 and if n is 4, R₇ is a group

R₈ is C₁-C₁₂alkyl, C₃-C₁₈alkenyl, C₃-C₂₀alkyl which is interrupted byone or more O and/or substituted by OH or R₈ is C₁-C₄alkyl which issubstituted by —P(O)(OR₁₄)₂, R₉ and R₁₀ are C₁-C₆alkyl or R₉ and R₁₀together are pentamethylene or 3-oxapentamethylene, R₁₁ is C₁-C₁₂alkyl,C₂-C₅alkenyl or phenyl, R₁₄ is C₁-C₁₄alkyl, R₁₅ is C₂-C₈alkylene,C₄-C₅₀alkylene which is interrupted by one or more O, or is a group

R₁₆ is C₂-C₈alkylene, C₂-C₆oxaalkylene or C₂-C₆thiaalkylene and R₁₈ isC₄-C₈alkyl C₄-C₁₂alkylene which is interrupted by one or more O.
 3. Anorganic material according to claim 1, wherein the triazine compound (b)is a compound of the formula I in which n is 1, 2 or 4, R₁ and R₂independently of one another are H or CH₃, R₃ and R₄ independently ofone another are H, CH₃ or Cl, R₅ and R₆ are hydrogen, R₇, if n is 1, isa) C₁-C₁₄alkyl which is substituted by one or more of the groups OH,C₁-C₁₅alkoxy, allyloxy, phenoxy, furyloxy,

—COOR₈, —CON(R₉)(R₁₀) and/or by —OCOR₁₁, b) C₆-C₄₅alkyl which isinterrupted by one or more O and can be substituted by OH or/andglycidyloxy, c) glycidyl or d) hydroxycyclohexyl,  and if n is 2, R₇ isC₆-C₁₂alkenylene, 2-butenylene-1,4, xylylene, C₃-C₂₀alkylene whichinterrupted by one or more O or substituted by OH, or R₇ is a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CO—R₁₆—CO—, —CH₂—COO—R₁₈—OOC—CH₂— or

 and if n is 4, R₇ is

R₈ is C₄-C₁₀alkyl, oleyl, C₃-C₂₀alkyl which is interrupted by one ormore O and/or substituted by OH, or R₈ is —CH₂P(O)(OR₁₄)₂, R₉ and R₁₀are C₂-C₆alkyl R₁₁ is C₆-C₁₀alkyl, C₂-C₃alkenyl R₁₄ is C₁-C₁₄alkyl, R₁₅is C₂-C₈alkylene, C₁₀-C₄₅alkylene which is interrupted by more than oneO, or is a group

R₁₆ is C₄-C₈alkylene and R₁₈ is C₄-C₈alkylene.
 4. An organic materialaccording to claim 1, wherein the component (b) is a compound of theformula I in which n is 1 or 2 and, if n is 1, R₇ is a group—CH₂CH(OH)CH₂—OR₂₁ in which R₂₁ is C₁-C₁₈alkyl, allyl, phenyl, furyl,C₆-C₁₂alkanoyl or C₃-C₅alkenoyl and, if n is 2, R₇ is a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂— in which R₁₅ is as defined in claim 1.5. An organic material according to claim 1, wherein the component (b)is a compound of the formula I in which R₁ and R₂ are hydrogen ormethyl, R₃ and R₄ are hydrogen, chlorine or methyl and R₅ and R₆ arehydrogen.
 6. An organic material according to claim 1, wherein thecomponent (a) is a compound containing at least one group of the formula

in which R is hydrogen or methyl.
 7. An organic material according toclaim 6, wherein R is hydrogen.
 8. An organic material according toclaim 6, wherein component (a) is selected from the group consisting ofdi-(2,2,6,6-tetramethylpiperidin-4-yl)succinate,di-(2,2,6,6-tetramethylpiperidin-4-yl)sebacate,di-(1,2,2,6,6-pentamethylpiperidin-4-yl)sebacate,di-(1,2,2,6,6-pentamethylpiperidin-4-yl)butyl-(3,5-di-tert-butyl-4-hydroxybenzyl)-malonate,di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate,tetra-(2,2,6,6-tetramethylpiperidin-4-yl)butane-1,2,3,4-tetracarboxylate,tetra-(1,2,2,6,6-pentamethylpiperidin-4-yl)butane-1,2,3,4-tetracarboxylate,N-(2,2,6,6-tetramethylpiperidin-4-yl)-β-aminopropionic acid dodecylester,N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N′-dodecyl-oxalamide,N-(2,2,6,6-tetramethylpiperidin-4-yl)-α-dodecylsuccinimide,2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]heneicosane,8-acetyl-3-dodecyl-1,3,8-triaza-7,7,9,9-tetramethylspiro[4.5]decane-2,4-dione,20-(dodecyloxycarbonylethyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxo-dispiro[5.1.11.2]heneicosane,

 in which m is from 2 to about
 200. 9. An organic material according toclaim 1, which contains 0.01 to 5% by weight of the component (a) and0.02 to 5% by weight of the component (b), relative to the material. 10.An organic material according to claim 9, which contains 0.02 to 2% byweight of the component (a) and 0.05 to 3% by weight of the component(b).
 11. An organic material according to claim 1, wherein the materialis an organic polymer.
 12. An organic polymer according to claim 11,which, in addition to the components (a) and (b) also contains furtherstabilizers, fillers, reinforcing agents, pigments, dyes, plasticizers,solvents, lubricants, flow-control agents, fluorescent brighteners,nucleating agents, antistatic agents or fire-retarding agents.
 13. Anorganic polymer according to claim 11, wherein the polymer is a coatingbinder.
 14. An organic material according to claim 1, wherein thematerial is a radiation-curable coating material.
 15. Aradiation-curable coating material containing ano-hydroxyphenyl-s-triazine compound of formula I as defined in claim 1.16. A process for stabilizing organic material against damage caused bylight, heat and oxygen, which process comprises incorporating into saidorganic material components (a) and (b) as defined in claim
 1. 17. Acompound of the formula Ia

in which n is 1 to 4, R₁ and R₂ independently of one another are H, OH,C₁-C₁₂alkyl, cyclohexyl or trifluoromethyl, R₃ and R₄ independently ofone another are H, OH, C₁-C₁₂alkyl, cyclohexyl, C₁-C₁₈alkoxy or halogenand, in the event that n=1, can also be a radical —OR₇, R₅ and R₆independently of one another are H, C₁-C₁₂alkyl or halogen, R₇, if n is1, is a) C₁-C₁₂alkyl which is substituted by phenoxy (which isunsubstituted or substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen) orby a group —COOR₈, —CONH₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, NHR₉,—N(R₉)(R₁₀) or —O—CO—R₂₂, b) C₄-C₅₀alkyl which is interrupted by morethan one O and can be substituted by OH or/and glycidyloxy, c) glycidylor a group

d) cyclohexyl substituted by OH or —OCOR₁₁ e) a group —CH₂CH(OH)CH₂OR₂₁f) a group —SO₂—R₁₃, g) a group —CO—R₁₂  and if n is 2, R₇ is a)C₂-C₁₂alkylene, b) C₄-C₁₂alkenylene, c) xylylene, d) C₃-C₂₀alkylenewhich is interrupted by one or more O and/or substituted by OH, e) agroup —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—,—(CH₂)_(m)—COO—R₁₈—OOC—(CH₂)_(m)— (wherein m is 1-3) or

 and if n is 3, R₇ is a group

 (wherein m is 1-3),  and if n is 4, R₇ is a group

 (wherein m is 1-3), R₈ is C₃-C₂₀alkyl which is interrupted by one ormore O, N or S and can be substituted by OH, or R₈ is C₁-C₄alkyl whichis substituted by —P(O)(OR₁₄)₂, —N(R₉)(R₁₀), or —OCOR₁₁ and/or OH, or R₈is C₃-C₁₈alkenyl, glycidyl or C₇-C₁₁phenylalkyl, R₉ and R₁₀independently are C₁-C₁₂alkyl, C₃-C₁₂alkoxyalkyl,C₄-C₁₆dialkylaminoalkyl or C₅-C₁₂cycloalkyl, or R₉ and R₁₀ together areC₃-C₉alkylene or C₃-C₉oxaalkylene or C₃-C₉azaalkylene, R₁₁ isC₁-C₁₈alkyl, C₂-C₁₈alkenyl or phenyl, R₁₂ is a group —R₂₄—COOH or—NH—R₁₇—NCO, R₁₃ is C₁-C₁₂alkyl, C₆-C₁₂aryl or C₇-C₁₄alkaryl R₁₄ isC₁-C₁₂alkyl or phenyl R₁₅ is C₂-C₁₀alkylene, C₄-C₅₀alkylene which isinterrupted by one or more O, or R₁₅ is phenylene or a group-phenylene-X-phenylene in which X is —O—, —S—, —SO₂—, —CH₂— or—C(CH₃)₂—, R₁₇ is C₂-C₁₀alkylene, phenylene, tolylene,diphenylenemethane or a group

R₁₈ is C₂-C₁₀alkylene or C₄-C₂₀alkylene which is interrupted by one ormore O, R₁₉ is C₃-C₁₂alkanetriyl, R₂₀ is C₄-C₁₂alkanetetryl, R₂₁ is H,C₁-C₁₈alkyl, C₃-C₁₈alkenyl, phenyl, phenyl substituted by C₁-C₁₂alkyl,C₁-C₁₂alkoxy or halogen, or R₂₁ is C₂-C₁₈alkanoyl, benzoyl,C₃-C₁₈alkenoyl, furyl or a group

R₂₂ is C₂-C₅alkenyl, R₂₃ is C₂-C₁₀alkylene, phenylene or a group

 wherein X is O, S, SO₂, CH₂ or C(CH₃)₂, and R₂₄ is C₂-C₁₄alkylene,vinylene or o-phenylene.
 18. A compound of the formula Ia according toclaim 17, in which n is 1 or 2, R₁ and R₂ independently of one anotherare H, OH, C₁-C₁₂alkyl or halogenomethyl, R₃ and R₄ independently of oneanother are H, OH, C₁-C₁₂alkyl, C₁-C₁₈alkoxy or halogen and, in theevent that n=1, can also be a radical —OR₇, R₅ and R₆ independently ofone another are H, C₁-C₁₂alkyl or halogen, R₇ is C₁-C₁₂alkyl which issubstituted by phenoxy which is unsubstituted or substituted byC₁-C₁₈alkyl, C₁-C₁₈alkoxy or halogen, C₁-C₁₂alkyl which is substitutedby —COOR₈, —CONH₂, —CONHR₉, —CON(R₉)(R₁₀), —NH₂, —NHR₉ or —N(R₉)(R₁₀),C₆-C₂₀alkyl which is interrupted by more than one O and is substitutedby OH, glycidyl, cyclohexyl substituted by OH or —OCOR₁₁, a group—CH₂CH(OH)CH₂OR₁₉ or —SO₂R₁₃, if n is 1, and, if n is 2, isC₂-C₁₂alkylene, C₄-C₁₂alkenylene, xylylene, C₃-C₂₀alkylene which isinterrupted by O and/or substituted by OH, or a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂— or —(CH₂)_(m)—COO—R₁₈—OOC—(CH₂)_(m)—in which m is 1-3, R₈ is C₃-C₂₀alkyl which is interrupted by O, N or Sand/or substituted by OH, C₁-C₄alkyl which is substituted by—P(O)(OR₁₄)₂, —N(R₉)(R₁₀) or —OCOR₁₁ and/or —OH, C₃-C₁₈alkenyl, glycidylor C₇-C₁₁phenylalkyl, R₉ and R₁₀ independently of one another areC₁-C₁₂alkyl, C₃-C₁₂alkoxyalkyl, C₄-C₁₆di-alkylaminoalkyl orC₅-C₁₂cycloalkyl, or R₉ and R₁₀ together are C₃-C₉alkylene orC₃-C₉oxaalkylene or C₃-C₉azaalkylene, R₁₁ is C₁-C₁₈alkyl, C₂-C₁₆alkenylor phenyl, R₁₃ is C₁-C₁₂alkyl, C₆-C₁₂aryl or C₇-C₁₄alkaryl, R₁₄ isC₁-C₁₂alkyl or phenyl, R₁₅ is C₂-C₁₀alkylene, phenylene or a group-phenylene-X-phenylene in which X is —O—, —S—, —SO₂—, —CH₂— or —C(CH₃)₂,R₁₈ is C₂-C₁₀alkylene or C₄-C₂₀akylene which is interrupted by O, andR₁₉ is C₁-C₁₈alkyl, phenyl, phenyl which is substituted by C₁-C₁₂alkyl,C₁-C₁₂alkoxy or halogen, C₂-C₁₂alkanoyl, benzoyl or C₃-C₅alkenoyl.
 19. Acompound according to claim 17 of the formula Ia in which n is 1 to 4,R₁ and R₂ independently of one another are H, OH or C₁-C₄alkyl, R₃ andR₄ independently of one another are H, OH, C₁-C₄alkyl, C₁-C₄alkoxy,halogen or a radical —OR₇, R₅ and R₆ independently of one another are Hor C₁-C₄alkyl, R₇, if n is 1, is C₁-C₆alkyl which is substituted by—COOR₈, —COONH , —CON(R₉)(R₁₀) or —OCOR₂₂, or R₇ is glycidyl,hydroxycyclohexyl or a group —CH₂CH(OH)CH₂OR₂₁, and if n is 2, R₇ isC₄-C₁₂alkylene, C₄-C₆alkenylene, xylylene, C₃-C₂₀alkylene which isinterrupted by one or more O and/or substituted by OH, or R₇ is a group—CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CH₂—COO—R₁₈—OOCCH₂— or

and if n is 3, R₇ is a group

and if n is 4, R₇ is a group

R₈ is C₃-C₂₀alkyl which is interrupted by one or more O and can besubstituted by OH or R₈ is C₁-C₄alkyl which is substituted by—P(O)(OR₁₄)₂ or R₈ is C₃-C₁₈alkenyl, R₉ and R₁₀ independently areC₁-C₈alkyl or cyclohexyl or R₉ and R₁₀ together are pentamethylene or3-oxapentamethylene, R₁₄ is C₁-C₁₄alkyl, R₁₅ is C₂-C₈alkylene,C₄-C₅₀alkylene which is interrupted by one or more O, or R₁₅ is a group-phenylene-X-phenylene- in which X is —O—, —CH₂— or —C(CH₃)₂—, R₁₈ isC₄-C₈alkylene or C₄-C₁₂alkylene which is interrupted by one or more O,R₂₁ is H, C₄-C₁₈alkyl, allyl, phenyl, furyl, C₅-C₁₉alkanoyl orC₃-C₅alkenoyl and R₂₂ is C₂-C₅alkenyl.
 20. A compound according to claim17 of the formula Ia in which n is 1 or 2, R₁ and R₂ independently ofone another are H or CH₃, R₃ and R₄ independently of one another are H,CH₃ or Cl, R₅ and R₆ are hydrogen, R₇, if n is 1, is C₁-C₄alkyl which issubstituted by —COOR₈, —CON(R₉)(R₁₀) or —O—COR₂₂, or R₇ is glycidyl,2-hydroxycyclohexyl or a group —CH₂CH(OH)CH₂OR₂₁, and if n is 2, R₇ isC₆-C₁₂alkenylene, 2-butene-1,4-ylene, xylylene or C₃-C₂₀alkylene whichis interrupted by one or more O and/or substituted by OH, or R₇ is agroup —CH₂CH(OH)CH₂O—R₁₅—OCH₂CH(OH)CH₂—, —CH₂—COO—R₁₈—OOCCH₂— or

and if n is 4, R₇ is a group

R₈ is C₃-C₂₀alkyl which is interrupted by one or more O and can besubstituted by OH or R₈ is —CH₂P(O)(OR₁₄)₂ or oleyl R₉ and R₁₀ areC₂-C₆alkyl R₁₅ is C₂-C₈alkylene, C₁₀-C₄₅alkylene which is interrupted byone or more O or is a group

R₁₈ is C₄-C₈alkylene, R₂₁ is H, C₄-C₁₅alkyl, allyl, phenyl, furyl,C₅-C₁₂alkanoyl or C₃-C₅alkenoyl and R₂₂ is C₂-C₃alkenyl.
 21. A compoundaccording to claim 17 of the formula Ia in which n is
 2. 22. A processfor stabilizing organic material against damage caused by light, heatand oxygen, which process comprises incorporating into said organicmaterial at least one o-hydroxyphenyl-s-triazine compound of the formulaIa according to claim
 17. 23. An organic material containing at leastone compound of the formula Ia according to claim 17 as a stabilizeragainst damage caused by light, heat and oxygen.
 24. An organic polymeras a material according to claim
 23. 25. An organic material accordingto claim 23, containing 0.01 to 10% by weight of a compound of theformula Ia, relative to the material.
 26. A polycarbonate according toclaim
 24. 27. An organic material according to claim 23 which is aradiation-curable coating material.